This invention relates to novel heterocycles including 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzylo xycarbonylamino)propionic acid, which are useful as antagonists of the .alpha..sub.v .beta..sub.3 integrin and related cell surface adhesive protein receptors, to pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of cell adhesion, the treatment of angiogenic disorders, inflammation, bone degradation, cancer metastasis, diabetic retinopathy, thrombosis, restenosis, macular degeneration, and other conditions mediated by cell adhesion and/or cell migration and/or angiogenesis.

Description

381 parts

›FIELD OF THE INVENTION

This application claims priority under 35 U.S.C. 119 (e) from provisional application Ser. No. 60/009,088, filed Dec. 22, 1995 and 60/025,699 filed Aug. 9, 1996.

This invention relates to novel heterocycles which are useful as antagonists of the α v β 3 integrin and related cell surface adhesive protein receptors, to pharmaceutical compositions containing such compounds, processes for preparing such compounds, and to methods of using these compounds, alone or in combination with other therapeutic agents, for the inhibition of cell adhesion, the treatment of angiogenic disorders, inflammation, bone degradation, cancer metastasis, diabetic retinopathy, thrombosis, restenosis, macular degeneration, and other conditions mediated by cell adhesion and/or cell migration and/or angiogenesis.

›BACKGROUND OF THE INVENTION · 1 of 2

Angiogenesis or neovascularization is critical for normal physiological processes such as embryonic development and wound repair (Folkman and Shing, J. Biol. Chem. 1992, 26:10931-10934; D'Amore and Thompson, Ann. Rev. Physiol. 1987, 49:453-464). However, angiogenesis also occurs pathologically, for example, in ocular neovascularization (leading to diabetic retinopathy, neovascular glaucoma, retinal vein occlusion and blindness), in rheumatoid arthritis and in solid tumors (Folkman and Shing, J. Biol. Chem., 1992, 267:10931-10934; Blood and Zetter, Biochim. Biophys. Acta., 1990, 1032:118-128).

Tumor dissemination, or metastasis, involves several distinct and complementary components, including the penetration and traversing of tumor cells through basement membranes and the establishment of self-sustaining tumor foci in diverse organ systems. To this end, angiogenesis is critical to tumor survival. Without neovascularization, tumor cells lack the nourishment to divide and will not be able to leave the primary tumor site (Folkman and Shing, J. Biol. Chem., 1992, 267:10931-10934).

Inhibition of angiogenesis in animal models of cancer has been shown to result in tumor growth suppression and prevention of metastatic growth (Herblin et al., Exp. Opin. Ther. Patents, 1994, 1-14). Many angiogenic inhibitors have been directed toward blocking initial cytokine-dependent induction of new vessel growth, e.g. antibodies to endothelial cell growth factors. However, these approaches are problematic because tumor and inflammatory cells can secrete multiple activators of angiogenesis (Brooks et al., Cell, 1994, 79:1157-1164). Therefore, a more general approach that would allow inhibition of angiogenesis due to a variety of stimuli would be of benefit.

The integrin α v β 3 , sometimes called the vitronectin receptor, is preferentially expressed on angiogenic blood vessels in chick and man (Brooks et al., Science, 1994, 264:569-571; Enenstein and Kramer, J. Invest. Dermatol., 1994, 103:381-386). α v β 3 is the most promiscuous member of the integrin family, allowing endothelial cells to interact with a wide variety of extracellular matrix components (Hynes, Cell, 1992, 69:11-25). These adhesive interactions are considered to be critical for angiogenesis since vascular cells must ultimately be capable of invading virtually all tissues.

While integrin α v β 3 promotes adhesive events important for angiogenesis, this receptor also transmits signals from the extracellular environment to the intracellular compartment (Leavesley et al., J. Cell Biol., 1993, 121:163-170, 1993). For example, the interaction between the α v β 3 integrin and extracellular matrix components promotes a calcium signal required for cell motility.

During endothelium injury, the basement membrane zones of blood vessels express several adhesive proteins, including but not limited to von Willebrand factor, fibronectin, and fibrin. Additionally, several members of the integrin family of adhesion receptors are expressed on the surface of endothelial, smooth muscle and on other circulating cells. Among these integrins is α v β 3 , the endothelial cell, fibroblast, and smooth muscle cell receptor for adhesive proteins including von Willebrand factor, fibrinogen (fibrin), vitronectin, thrombospondin, and osteopontin. These integrins initiate a calcium-dependent signaling pathway that can lead to endothelial cell and smooth muscle cell migration and, therefore, may play a fundamental role in vascular cell biology.

Recently, an antibody to the α v β 3 integrin has been developed that inhibits the interaction of this integrin with agonists such as vitronectin (Brooks et al., Science, 1994, 264:569-571). Application of this antibody has been shown to disrupt ongoing angiogenesis on the chick chorioallantoic membrane (CAM), leading to rapid regression of histologically distinct human tumor transplanted onto the CAM (Brooks et al., Cell, 1994, 79:1157-1164). In this model, antagonists of the α v β 3 integrin induced apoptosis of the proliferating angiogenic vascular cells, leaving pre-existing quiescent blood vessels unaffected. Thus, α v β 3 integrin antagonists have been shown to inhibit angiogenesis and are recognized as being useful as therapeutic agents for the treatment of human diseases such as cancer, restenosis, thromoembolic disorders, rheumatoid arthritis and ocular vasculopathies (Folkman and Shing, J. Biol. Chem., 1992, 267:10931-10934).

Increasing numbers of other cell surface receptors have been identified which bind to extracellular matrix ligands or other cell adhesion ligands thereby mediating cell-cell and cell-matrix adhesion processes. Like the α v β 3 integrin, these receptors belong to the integrin gene superfamily and are composed of heterodimeric transmembrane glycoproteins containing α- and β-subunits. Integrin subfamilies contain a common β-subunit combined with different α-subunits to form adhesion receptors with unique specificity. The genes for eight distinct β-subunits have been cloned and sequenced to date.

The integrin α v β 3 is a member of the β 3 integrin subfamily and has been described on platelets, endothelial cells, melanoma, smooth muscle cells, and osteoclasts (Horton and Davies, J. Bone Min. Res. 1989, 4:803-808; Davies et al., J. Cell. Biol. 1989, 109:1817-1826; Horton, Int. J. Exp. Pathol., 1990, 71:741-759). Like the major platelet integrin GPIIb/IIIa, the vitronectin receptor binds a variety of RGD-containing adhesive proteins such as vitronectin, fibronectin, von Willibrand factor, fibrinogen, osteopontin, bone sialoprotein II and thrombospondin in a manner mediated by the RGD sequence.

A key event in bone resorption is the adhesion of osteoclasts to the matrix of bone. Studies with monoclonal antibodies have implicated the α v β 3 receptor in this process and suggest that a selective α v β 3 antagonist would have utility in blocking bone resorption in diseases such as osteoporosis (Horton et al., J. Bone Miner. Res., 1993, 8:239-247; Helfrich et al., J. Bone Miner. Res., 1992, 7:335-343).

›BACKGROUND OF THE INVENTION · 2 of 2

PCT Patent Application Publication Number WO94/08962, published Apr. 28, 1994 discloses fibrinogen receptor antagonists of the general formula shown below: ##STR1##

European Patent Application Publication Number 655,439, published May 31, 1995 discloses fibrinogen receptor antagonists of the general formula shown below: ##STR2##

PCT Patent Application Publication Number WO95/17397, published Jun. 29, 1995, discloses fibrinogen receptor antagonists of the general formula shown below: ##STR3##

PCT Patent Application Publication Number WO96/20192, published Jul. 4, 1996, discloses fibrinogen receptor antagonists of the general formula shown below: ##STR4##

Co-pending, commonly assigned U.S. patent application Ser. No. 08/455,768 filed May 31, 1995 discloses integrin inhibitors of the general formula shown below: ##STR5##

None of the above references discloses or suggests the compounds of the present invention which are described in detail below.

›SUMMARY OF THE INVENTION

The present invention provides novel nonpeptide compounds which bind to integrin receptors thereby altering cell-matrix and cell-cell adhesion processes. The compounds of the present invention are useful for the inhibition of cell adhesion and the treatment (including prevention) of angiogenic disorders, inflammation, bone degradation, cancer metastases, diabetic retinopathy, thrombosis, restenosis, macular degeneration, and other conditions mediated by cell adhesion and/or cell migration and/or angiogenesis.

One aspect of this invention provides novel compounds of Formula Ia, Ib or Ic (described below) which are useful as antagonists of the α v β 3 integrin. The α v β 3 integrin is also referred to as the α v β 3 receptor or the vitronectin receptor. The compounds of the present invention inhibit the binding of vitronectin or other RGD-containing ligands to α v β 3 and inhibit cell adhesion. The present invention also includes pharmaceutical compositions containing such compounds, and methods of using such compounds for the inhibition of angiogenesis, and/or for the treatment of disorders mediated by angiogenesis.

Another aspect of the present invention comprises agents that inhibit the binding of vitronectin to the α v β 3 receptor for the treatment (including prevention) of thrombosis, which do not significantly alter hemostatic balance and do not significantly inhibit platelet aggregation and do not significantly inhibit coagulation. Also, the compounds of the current invention can be used for the treatment or prevention of restenosis.

The present invention also provides novel compounds, pharmaceutical compositions and methods which may be used in the treatment or prevention of other diseases which involve cell adhesion processes, including, but not limited to, rheumatoid arthritis, asthma, allergies, adult respiratory distress syndrome, graft versus host disease, organ transplantation, septic shock, psoriasis, eczema, contact dermatitis, osteoporosis, osteoarthritis, atherosclerosis, metastasis, wound healing, diabetic retinopathy, ocular vasculopathies, inflammatory bowel disease and other autoimmune diseases.

Also included in the present invention are pharmaceutical kits comprising one or more containers containing pharmaceutical dosage units comprising a compound of Formula Ia, Ib or Ic, for the therapeutic inhibition of cell adhesion, the treatment of angiogenic disorders, inflammation, bone degradation, cancer metastasis, diabetic retinopathy, thrombosis, restenosis, macular degeneration, and other conditions mediated by cell adhesion and/or cell migration and/or angiogenesis.

›DETAILED DESCRIPTION OF THE INVENTION · 1 of 21

The present invention provides novel compounds of Formula Ia, Ib or Ic (described below) which bind to integrin receptors thereby altering cell-matrix and cell-cell adhesion processes. The compounds of the present invention are useful for the inhibition of cell adhesion and the treatment of angiogenic disorders, inflammation, bone degradation, cancer metastases, diabetic retinopathy, thrombosis, restenosis, macular degeneration, and other conditions mediated by cell adhesion and/or cell migration and/or angiogenesis, in a mammal.

One aspect of this invention provides novel compounds of Formula Ia, Ib or Ic (described below) which are. useful as antagonists of the α v β 3 integrin. The α v β 3 integrin is also referred to as the α v β 3 receptor or the vitronectin receptor. The compounds of the present invention inhibit the binding of vitronectin or other RGD-containing ligands to α v β 3 and inhibit cell adhesion. The present invention also includes pharmaceutical compositions containing such compounds of Formula Ia, Ib or Ic, and methods of using such compounds for the inhibition of angiogenesis, and/or for the treatment of angiogenic disorders, inflammation, bone degradation, cancer metastases, diabetic retinopathy, thrombosis, restenosis, macular degeneration, and other conditions mediated by cell adhesion and/or cell migration and/or angiogenesis, in a mammal.

1! One aspect of the present invention comprises compounds of Formula Ia: ##STR6## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof, wherein:

X 1 , X 2 , X 3 , and X 4 are independently selected from nitrogen or carbon provided that at least two of X 1 , X 2 , X 3 and X 4 are carbon; R 1 is selected from: ##STR7## A and B are independently --CH 2 --, --O--, --N(R 2 )--, or --C(═O)--;

A 1 and B 1 are independently --CH 2 -- or --N(R 3 )--;

D is --N(R 2 )--, --O--, --S--, --C(═O)-- or --SO 2 --;

E--F is --C(R 4 )═C(R 5 )--, --N═C(R 4 )--, --C(R 4 )═N--, or --C(R 4 ) 2 C(R 5 ) 2 --;

J, K, L and M are independently selected from --C(R 4 )--, --C(R 5 )-- or --N--, provided that at least one of J, K, L and M is not --N--;

R 2 is selected from: H, C 1 -C 6 alkyl, (C 1 -C 6 alkyl)carbonyl, (C 1 -C 6 alkoxy)carbonyl; (C 1 -C 6 alkyl)aminocarbonyl, C 3 -C 6 alkenyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, heteroaryl(C 1 -C 6 alkyl)carbonyl, heteroarylcarbonyl, aryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)carbonyl--, arylcarbonyl, C 1 -C 6 alkylsulfonyl, arylsulfonyl, aryl(C 1 -C 6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C 1 -C 6 alkyl)sulfonyl, aryloxycarbonyl, or aryl(C 1 -C 6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo, CF 3 , and nitro;

R 3 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

R 4 and R 5 are independently selected from: H, C 1 -C 4 alkoxy, NR 2 R 3 , halogen, NO 2 , CN, CF 3 , C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)carbonyl, (C 1 -C 6 alkoxy)carbonyl, arylcarbonyl, or

alternatively, when substituents on adjacent atoms, R 4 and R 5 can be taken together with the carbon atoms to which they are attached to form a 5-7 membered carbocyclic or 5-7 membered heterocyclic aromatic or non-aromatic ring system, said carbocyclic or heterocyclic ring being optionally substituted with 0-2 groups selected from: C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo, cyano, amino, CF 3 , or NO 2 ;

U is selected from:

--(CH 2 ) n --,

--(CH 2 ) n (CR 7 ═CR 8 )(CH 2 ) m --,

--(CH 2 ) n (C.tbd.C)(CH 2 ) m --,

--(CH 2 ) t Q(CH 2 ) m --,

--(CH 2 ) n O(CH 2 ) m --,

--(CH 2 ) n N(R 6 )(CH 2 ) m --,

--(CH 2 ) n C(═O)(CH 2 ) m --,

--(CH 2 ) n (C═O)N(R 6 )(CH 2 ) m --

--(CH 2 ) n N(R 6 )(C═O)(CH 2 ) m --, or

--(CH 2 ) n S(O) p (CH 2 ) m --;

wherein one or more of the methylene groups in U is optionally substituted with R 7 ;

Q is selected from 1,2-cycloalkylene, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, 2,4-pyridinylene, or 3,4-pyridazinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl; R 7 and R 8 are independently selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 0 -C 6 alkyl)-;

R 10 is selected from: H, C 1 -C 4 alkoxy substituted with 0-1 R 21 , N(R 6 ) 2 , halogen, NO 2 , CN, CF 3 , CO 2 R 17 , C(═O)R 17 , CONR 17 R 20 , --SO 2 R 17 , --SO 2 NR 17 R 20 , C 1 -C 6 alkyl substituted with 0-1 R 15 or 0-1 R 21 , C 3 -C 6 alkenyl substituted with 0-1 R 15 or 0-1 R 21 , C 3 -C 7 cycloalkyl substituted with 0-1 R 15 or 0-1 R 21 , C 4 C 11 cycloalkylalkyl substituted with 0-1 R 15 or 0-1 R 21 , aryl substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 , or aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 ;

R 11 is selected from H, halogen, CF 3 , CN, NO 2 , hydroxy, NR 2 R 3 , C 1 -C 4 alkyl substituted with 0-1 R 21 , C 1 -C 4 alkoxy substituted with 0-1 R 21 , aryl substituted with 0-1 R 21 , aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 21 , (C 1 -C 4 alkoxy)carbonyl substituted with 0-1 R 21 , (C 1 -C 4 alkyl)carbonyl substituted with 0-1 R 21 , C 1 -C 4 alkylsulfonyl substituted with 0-1 R 21 , or C 1 -C 4 alkylaminosulfonyl substituted with 0-1 R 21 ;

W is selected from:

--(C(R 12 ) 2 ) q C(═O)N(R 13 )--, or --C(═O)--N(R 13 )--(C(R 12 ) 2 ) q --;

X is --C(R 12 )(R 14 )--C(R 12 )(R 15 )--; or

alternatively, W and X can be taken together to be ##STR8## R 12 is selected from H, halogen, C 1 -C 6 alkyl C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 10 cycloalkylalkyl, (C 1 -C 4 alkyl)carbonyl, aryl, or aryl(C 1 -C 6 alkyl)-;

R 13 is selected from H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkylmethyl, or aryl(C 1 -C 6 alkyl)-;

R 14 is selected from:

H, C 1 -C 6 alkylthio (C 1 -C 6 alkyl)-, aryl(C 1 -C 10 alkylthioalkyl)-, aryl(C 1 -C 10 alkoxyalkyl)-, C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl 1 C 3 -C 10 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O) R 17 , or CONR 17 R 20 , provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-1 R 16 or 0-2 R 11 ;

›DETAILED DESCRIPTION OF THE INVENTION · 2 of 21

R 15 is selected from:

H, R 16 , C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 10 alkylaminoalkyl, C 1 -C 10 dialkylaminoalkyl, (C 1 -C 10 alkyl)carbonyl, aryl(C 0 -C 6 alkyl)carbonyl, C 1 -C 10 alkenyl, C 1 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O)R 17 , CONR 17 R 20 , SO 2 R 17 , or SO 2 NR 17 R 20 , provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-2 R 11 ;

Y is selected from:

--COR 19 , --SO 3 H, --PO 3 H, tetrazolyl, --CONHNHSO 2 CF 3 , --CONHSO 2 R 17 , --CONHSO 2 NHR 17 , --NHCOCF 3 , --NHCONHSO 2 R 17 , --NHSO 2 R 17 , --OPO 3 H 2 , --OSO 3 H, --PO 3 H 2 , --SO 3 H, SO 2 NHCOR 17 , --SO 2 NHCO 2 R 17 , ##STR9## R 16 is selected from: --N(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --NR 20 R 17 ;

R 17 is selected from:

--C 1 -C 10 alkyl, C 3 -C 11 cycloalkyl, aryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)aryl, heteroaryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)heteroaryl, biaryl(C 1 -C 6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C 1 -C 4 alkyl, C 1 -C 4 alkoxy, aryl, heteroaryl, halo,cyano, amino, CF 3 , and NO 2 ;

R 18 is selected from:

H, --C(═O)--O--R 17 , --C(═O)--R 17 , --C(═O)--NH--R 17 , --SO 2 --R 17 , or --SO 2 --NR 20 R 17 ;

R 19 is selected from: hydroxy, C 1 -C 10 alkyloxy, C 3 -C 11 cycloalkyloxy, aryloxy, aryl(C 1 -C 6 alkoxy)- , C 3 -C 10 alkylcarbonyloxyalkyloxy, C 3 -C 10 alkoxycarbonyloxyalkyloxy, C 2 -C 10 alkoxycarbonylalkyloxy, C 5 -C 10 cycloalkylcarbonyloxyalkyloxy, C 5 -C 10 cycloalkoxycarbonyloxyalkyloxy, C 5 -C 10 cycloalkoxycarbonylalkyloxy, C 7 -C 11 aryloxycarbonylalkyloxy, C 8 -C 12 aryloxycarbonyloxyalkyloxy, C 8 -C 12 arylcarbonyloxyalkyloxy, C 5 -C 10 alkoxyalkylcarbonyloxyalkyloxy, C 5 -C 10 (5alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C 10 -C 14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R 11 )(R 12 )N--(C 1 -C 10 alkoxy)-;

R 20 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

R 21 is selected from: COOH or NR 6 2 ;

m is 0-4;

n is 0-4;

t is 0-4;

p is 0-2;

q is 0-2; and

r is 0-2;

with the following provisos:

(1) t, n, m and q are chosen such that the number of atoms connecting R 1 and Y is in the range of 10-14; and

(2) n and m are chosen such that the value of n plus m is greater than one unless U is --(CH 2 ) t Q(CH 2 ) m --.

2! Preferred compounds of the invention as described above are compounds of the Formula Ia: ##STR10## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof, wherein:

X 1 , X 2 , X 3 , and X 4 are independently selected from nitrogen or carbon provided that at least two of X 1 , X 2 , X 3 and X 4 are carbon;

R 1 is selected from: ##STR11## A and B are independently --CH 2 --, --O--, --N(R 2 )--, or --C(═O)--;

A 1 and B 1 are independently --CH 2 -- or --N(R 3 )--;

D is --N(R 2 )--, --O--, --S--, --C(═O)-- or --SO 2 --;

E--F is --C(R 4 )═C(R 5 )--, --N═C(R 4 )--, --C(R 4 )═N--, or --C(R 4 ) 2 (R 5 ) 2 --;

J, K, L and M are independently selected from --C(R 4 )--, --C(R 5 )-- or --N--, provided that at least one of J, K, L and M is not --N--;

R 2 is selected from: H, C 1 -C 6 alkyl, (C 1 -C 6 alkyl)carbonyl, (C 1 -C 6 alkoxy)carbonyl, C 1 -C 6 alkylaminocarbonyl, C 3 -C 6 alkenyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, heteroaryl(C l -C 6 alkyl)carbonyl, heteroarylcarbonyl, aryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)carbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, aryl(C 1 -C 6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C 1 -C 6 alkyl)sulfonyl, aryloxycarbonyl, or aryl(C 1 -C 6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo, CF 3 , and nitro;

R 3 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

U is selected from:

--(CH 2 ) n --,

--(CH 2 ) n (CR 7 ═CR 8 )(CH 2 ) m --,

--(CH 2 ) t Q(CH 2 ) m --,

--(CH 2 ) n O(CH 2 ) m --,

--(CH 2 ) n N(R 6 )(CH 2 ) m --,

--(CH 2 ) n C(═O)(CH 2 ) m --, or

--(CH 2 ) n S(O) p (CH 2 ) m --;

wherein one or more of the methylene groups in U is optionally substituted with R 7 ;

Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyyrdinylene, or 2,4-pyridinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl;

R 7 and R 8 are independently selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 0 -C 6 alkyl)-;

R 10 is selected from: H, C 1 -C 4 alkoxy substituted with 0-1 R 21 , N(R 6 ) 2 , halogen, NO 2 , CN, CF 3 , CO 2 R 17 , C(═O)R 17 , CONR 17 R 20 , --SO 2 R 17 , --SO 2 NR 17 R 20 , C 1 -C 6 alkyl substituted with 0-1 R 15 or 0-1 R 21 , C 3 -C 6 alkenyl substituted with 0-1 R 15 or 0-1 R 21 C 3 -C 7 cycloalkyl substituted with 0-1 R 15 or 0-1 R 21 , C 4 -C 11 cycloalkylalkyl substituted with 0-1 R 15 or 0-1 R 21 1 aryl substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 , or aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 ;

›DETAILED DESCRIPTION OF THE INVENTION · 3 of 21

R 11 is selected from: H, halogen, CF 3 , CN, NO 2 , hydroxy, NR 2 R 3 , C 1 -C 4 alkyl substituted with 0-1 R 21 , C 1 -C 4 alkoxy substituted with 0-1 R 21 , aryl substituted with 0-1 R 21 , aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 21 , (C 1 -C 4 alkoxy)carbonyl substituted with 0-1 R 21 , (C 1 -C 4 alkyl)carbonyl substituted with 0-1 R 21 C 1 -C 4 alkylsulfonyl substituted with 0-1 R 21 , or C 1 -C 4 alkylaminosulfonyl substituted with 0-1 R 21 ;

W is --C(═O)--N(R 13 )--(C(R 12 ) 2 ) q --;

X is --C(R 12 )(R 14 )--C(R 12 )(R 15 )--;

alternatively, W and X can be taken together to be ##STR12## R 12 is H or C 1 -C 6 alkyl; R 13 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkylmethyl, or aryl(C 1 -C 6 alkyl)-;

R 14 is selected from:

H, C 1 -C 6 alkylthioalkyl, aryl(C 1 -C 10 alkylthioalkyl)-, aryl(C 1 -C 10 alkoxyalkyl)-, C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O)R 17 , or CONR 17 R 20 , or provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be substituted independently with 0-1 R 16 or 0-2 R 11 ;

R 15 is selected from:

H, R 16 , C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 10 alkylaminoalkyl, C 1 -C 10 dialkylaminoalkyl, C 1 -C 10 alkylcarbonyl, aryl(C 0 -C 6 alkyl)carbonyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl ,C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O)R 17 , CONR 17 R 20 , SO 2 R 17 or SO 2 NR 17 R 20 , provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be substituted independently with 0-2 R 11 ;

Y is selected from: ##STR13## R 16 is selected from: --N(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --NR 20 R 17 ;

R 17 is selected from:

C 1 -C 10 alkyl, C 3 -C 11 cycloalkyl, aryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)aryl, heteroaryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)heteroaryl, biaryl(C 1 -C 6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C 1 -C 4 alkyl, C 1 -C 4 alkoxy, aryl, heteroaryl, halo,cyano, amino, CF 3 , and NO 2 ;

R 18 is selected from:

--C(═O)--O--R 17 ,

--C(═O)--R 17 ,

--C(═O)--NH--R 17 ,

--SO 2 --R 17 , or

--SO 2 --NR 20 R 17 ;

R 19 is selected from: hydroxy, C 1 -C 10 alkyloxy,

C 3 -C 11 cycloalkyloxy, C 6 -C 10 aryloxy,

C 7 -C 11 aralkyloxy, C 3 -C 10 alkylcarbonyloxyalkyloxy,

C 3 -C 10 alkoxycarbonyloxyalkyloxy,

C 2 -C 10 alkoxycarbonylalkyloxy,

C 5 -C 10 cycloalkylcarbonyloxyalkyloxy,

C 5 -C 10 cycloalkoxycarbonyloxyalkyloxy,

C 5 -C 10 cycloalkoxycarbonylalkyloxy,

C 7 -C 11 aryloxycarbonylalkyloxy,

C 8 -C 12 aryloxycarbonyloxyalkyloxy,

C 8 -C 12 arylcarbonyloxyalkyloxy,

C 5 -C 10 alkoxyalkylcarbonyloxyalkyloxy,

C 5 -C 10 (5-alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C 10 -C 14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R 11 )(R 12 )N--(C 1 -C 10 alkoxy)-;

R 20 selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

R 21 is selected from COOH or NR 6 2 ;

m is 0-4;

n is 0-4;

p is 0-2;

q is 0-2;

t is 0-4; and

r is 0-2.

3! Further preferred compounds of the invention as described above are compounds of the Formula IIa or IIb: ##STR14## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof wherein:

X 1 and X 3 are independently selected from nitrogen or carbon;

R 1 is selected from: ##STR15## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH 2 , halogen, NO 2 , CN, CF 3 , C 1 -C 4 alkoxy, C 1 -C 6 alkyl, and C 3 -C 7 cycloalkyl;

U is --(CH 2 ) n --, --(CH 2 ) t Q(CH 2 ) m -- or --C(═O)(CH 2 ) n-1 --, wherein one of the methylene groups is optionally substituted with R 7 ; Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyrrdinylene, or 2,4-pyridinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl;

R 7 is selected from: C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl), heteroaryl, or heteroaryl(C 1 -C 6 alkyl);

R 10 is selected from: H, C 1 -C 4 alkoxy substituted with 0-1 R 21 , halogen, CO 2 R 17 , CONR 17 R 20 , C 1 -C 6 alkyl substituted with 0-1 R 15 or 0-1 R 21 , C 3 -C 7 cycloalkyl substituted with 0-1 R 15 or 0-1 R 21 , C 4 -C 11 cycloalkylalkyl substituted with 0-1 R 15 or 0-1 R 21 , or aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 ;

R 11 is selected from: H, halogen, CF 3 , CN, NO 2 , hydroxy, NR 2 R 3 , C 1 -C 4 alkyl substituted with 0-1 R 21 , C 1 -C 4 alkoxy substituted with 0-1 R 21 , aryl substituted with 0-1 R 21 , aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 21 , (C 1 -C 4 alkoxy)carbonyl substituted with 0-1 R 21 , (C 1 -C 4 alkyl)carbonyl substituted with 0-1 R 21 , C 1 -C 4 alkylsulfonyl substituted with 0-1 R 21 , or C 1 -C 4 alkylaminosulfonyl substituted with 0-1 R 21 ;

W is --C(═O)--N(R 13 )--;

X is --CH(R 14 )--CH(R 15 )--;

R 13 is H or CH 3 ;

R 14 is selected from:

H, C 1 -C 10 alkyl, aryl, or heteroaryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C 1 -C 4 alkyl, C 1 -C 4 alkoxy, aryl, halo, cyano, amino, CF 3 , and NO 2 ;

R 15 is H or R 16 ;

Y is --COR 19 ;

R 16 is selected from:

--NH (R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --N(R 20 ) R 17 ;

R 17 is selected from:

›DETAILED DESCRIPTION OF THE INVENTION · 4 of 21

R 19 is selected from:

hydroxy, C 1 -C 10 alkoxy,

methylcarbonyloxymethoxy-,

ethylcarbonyloxymethoxy-,

t-butylcarbonyloxymethoxy-,

cyclohexylcarbonyloxymethoxy-,

1-(methylcarbonyloxy)ethoxy-,

1-(ethylcarbonyloxy)ethoxy-,

1-(t-butylcarbonyloxy)ethoxy-,

1-(cyclohexylcarbonyloxy)ethoxy-,

i-propyloxycarbonyloxymethoxy-,

t-butyloxycarbonyloxymethoxy-,

1-(i-propyloxycarbonyloxy)ethoxy-,

1-(cyclohexyloxycarbonyloxy)ethoxy-,

1-(t-butyloxycarbonyloxy)ethoxy-,

dimethylaminoethoxy-,

diethylaminoethoxy-,

(5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or

1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-;

R 20 is H or CH 3 ;

R 21 is selected from COOH or NR 6 2 ;

m is 0 or 1;

n is 1-4; and

t is 0 or 1.

4! Still further preferred compounds of the above invention are compounds of the Formula IIa or IIb: ##STR16## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof wherein: X 1 and X 3 are independently selected from nitrogen or carbon, provided that at least one of X 1 and X 3 is carbon;

R 1 is selected from: ##STR17## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH 2 , halogen, NO 2 , CN, CF 3 , C 1 -C 4 alkoxy, C 1 -C 6 alkyl, and C 3 -C 7 cycloalkyl;

U is --(CH 2 ) n --, --(CH 2 ) t Q (CH 2 ) m -- or --C(═O)(CH 2 ) n-1 --, wherein one of the methylene groups is optionally substituted with R 7 ;

Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl;

R7 is selected from: C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl), heteroaryl, or heteroaryl(C 1 -C 6 alkyl);

R 11 is selected from: H, halogen, CF 3 , CN, NO 2 , hydroxy, NR 2 R 3 , C 1 -C 4 alkyl substituted with 0-1 R 21 C 1 -C 4 alkoxy substituted with 0-1 R 21 , aryl substituted with 0-1 R 21 , aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 21 , (C 1 -C 4 alkoxy)carbonyl substituted with 0-1 R 21 , (C 1 -C 4 alkyl)carbonyl substituted with 0-1 R 21 , C 1 -C 4 alkylsulfonyl substituted with 0-1 R 21 , or C 1 -C 4 alkylaminosulfonyl substituted with 0-1 R 21 ;W is --C(═O)--N(R 13 )--;

W is --C(═O)-N(R 13 )--;

X is --CH(R 14 )--CH(R 15 )--;

R 13 is H or CH 3 ;

R 14 is selected from:

R 15 is H or R 16 ;

Y is --COR 19 ;

R 16 is selected from:

--N(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --NR 20 R 17 ;

R 17 is selected from:

R 19 is selected from:

hydroxy, C 1 -C 10 alkoxy,

methylcarbonyloxymethoxy-,

t-butylcarbonyloxymethoxy-,

cyclohexylcarbonyloxymethoxy-,

1-(methylcarbonyloxy)ethoxy-,

1-(ethylcarbonyloxy)ethoxy-,

1-(t-butylcarbonyloxy)ethoxy-,

1-(cyclohexylcarbonyloxy)ethoxy-,

i-propyloxycarbonyloxymethoxy-,

t-butyloxycarbonyloxymethoxy-,

1-(i-propyloxycarbonyloxy)ethoxy-,

1-(cyclohexyloxycarbonyloxy)ethoxy-,

1-(t-butyloxycarbonyloxy)ethoxy-,

dimethylaminoethoxy-,

diethylaminoethoxy-,

(5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or

1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-;

R 20 is H or CH 3 ;

R 21 is selected from COOH or NR 6 2 ;

m is 0 or 1;

n is 1-4; and

t is 0 or 1.

5! Specifically preferred compounds of the invention as described above are compounds of Formula Ia, including enantiomeric or diasteriomeric forms thereof, or mixtures of enantiomeric or diasteriomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof, selected from the group consisting of:

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzyloxycarbonylamino)-propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

›DETAILED DESCRIPTION OF THE INVENTION · 5 of 21

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 1-8 3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid, and

3- 1- 3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid.

›DETAILED DESCRIPTION OF THE INVENTION · 6 of 21

Also specifically preferred are ester prodrugs of the specifically preferred compounds of Formula Ia, said esters being chosen from the group consisting of:

methyl,

ethyl,

isopropyl,

n-butyl,

isobutyl,

benzyl,

methylcarbonyloxymethyl,

ethylcarbonyloxymethyl,

tert-butylcarbonyloxymethyl,

cyclohexylcarbonyloxymethyl,

tert-butyloxycarbonyloxymethyl,

dimethylaminoethyl,

diethylaminoethyl,

morpholinoethyl, pyrrolidinoethyl, and

trimethylanimonioethyl.

6! Another aspect of the present invention comprises compounds of Formula Ib: ##STR18## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof, wherein:

X 1 , X 2 , X 3 , and X 4 are independently selected from nitrogen or carbon provided that at least two of X 1 , X 2 , X 3 and X 4 are carbon;

R 1 is selected from: ##STR19## A and B are independently --CH 2 --, --O--, --N(R 2 )--, or --C(═O)--;

A 1 and B 1 are independently --CH 2 -- or --N(R 3 )--;

D is --N(R 2 )--, --O--, --S--, --C(═O)-- or --SO 2 --;

E--F is --C(R 4 )═C(R 5 )--, --N═C(R 4 )--, --C(R 4 )═N--, or --C(R 4 ) 2 C(R 5 ) 2 --;

J, K, L and M are independently selected from: --C(R 4 )--, --C(R 5 )-- or --N--, provided that at least one of J, K, L and M is not --N--;

R 2 is selected from: H, C 1 -C 6 alkyl, (C 1 -C 6 alkyl)carbonyl, (C 1 -C 6 alkoxy)carbonyl; (C 1 -C 6 alkyl)aminocarbonyl, C 3 -C 6 alkenyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, heteroaryl(C 1 -C 6 alkyl)carbonyl, heteroarylcarbonyl, aryl C 1 -C 6 alkyl, (C 1 -C 6 alkyl)carbonyl, or arylcarbonyl, C 1 -C 6 alkylsulfonyl, arylsulfonyl, aryl(C 1 -C 6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C 1 -C 6 alkyl)sulfonyl, aryloxycarbonyl, or aryl(C 1 -C 6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo, CF 3 , and nitro;

R 3 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroalry (C 1 -C 6 alkyl);

R 4 and R 5 are independently selected from: H, C 1 -C 4 alkoxy, NR 2 R 3 halogen, NO 2 , CN, CF 3 , C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)(C 1 -C 6 alkyl)carbonyl, (C 1 -C 6 alkoxy)carbonyl, arylcarbonyl, or

U is selected from:

--(CH 2 ) n --,

--(CH 2 ) n (CR 7 ═CR 8 )(CH 2 ) m --

--(CH 2 ) n (C.tbd.C)(CH 2 ) m --

--(CH 2 ) t Q(CH 2 ) m --

--(CH 2 ) n O(CH 2 ) m --,

--(CH 2 ) n N(R 6 )(CH 2 ) m --,

--(CH 2 ) n C(═O)(CH 2 ) m --,

--(CH 2 ) n (C═O)N(R 6 )(CH 2 ) m --

--(CH 2 ) n N(R 6 )(C═O)(CH 2 ) m --, or

--(CH 2 ) n S (O) p (CH 2 ) m --;

wherein one of the methylene groups is optionally substituted with R 7 ;

Q is selected from: 1,2-cycloalkylene, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, 2,4-pyridinylene, or 3,4-pyridazinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl;

R 7 and R 8 are independently selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 0 -C 6 alkyl)-;

R 9 is selected from: H, CO 2 R 17 , C(═O)R 17 , CONR 17 R 20 , --SO 2 R 17 , --SO 2 NR 17 R 20 , C 1 -C 6 alkyl substituted with 0-1 R 15 or 0-1 R 21 , C 3 -C 6 alkenyl substituted with 0-1 R 15 or 0-1 R 21 , C 3 -C 7 cycloalkyl substituted with 0-1 R 15 or 0-1 R 21 , C 4 -C 11 cycloalkylalkyl substituted with 0-1 R 15 or 0-1 R 21 , aryl substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 , or aryl(C 1 -C 6 alkyl)substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 ; R 11 is selected from H, halogen, CF 3 , CN, NO 2 , hydroxy, NR 2 R 3 , C 1 -C 4 alkyl substituted with 0-1 R 21 , C 1 -C 4 alkoxy substituted with 0-1 R 21 , aryl substituted with 0-1 R 21 , aryl(C 1 -C 6 alkyl)substituted with 0-1 R 21 , (C 1 -C 4 alkoxy)carbonyl substituted with 0-1 R 21 , (C 1 -C 4 alkyl)carbonyl substituted with 0-1 R 21 , C 1 -C 4 alkylsulfonyl substituted with 0-1 R 21 , or C 1 -C 4 alkylaminosulfonyl substituted with 0-1 R 21 ;

W is selected from:

--(C(R 12 ) 2 ) q C(═O)N(R 13 )--, or

--C(═O)--N(R 13 )--(C(R 12 ) 2 ) q --;

X is --C(R 12 )(R 14 )--C(R 12 )(R 15 )--; or

alternatively, W and X can be taken together to be ##STR20## R 12 is selected from: H, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 10 cycloalkylalkyl, (C 1 -C 4 alkyl)carbonyl, aryl, or aryl(C 1 -C 6 alkyl)-;

R 13 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkylmethyl, or aryl(C 1 -C 6 alkyl)-;

R 14 is selected from:

H, C 1 -C 6 alkylthio(C 1 -C 6 alkyl)-, aryl(C 1 -C 10 alkylthioalkyl)-, aryl(C 1 -C 10 alkoxyalkyl)-, C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O)R 17 , or CONR 17 R 20 , provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-1 R 16 or 0-2 R 11 ;

R 15 is selected from:

H, R 16 C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 10 alkylaminoalkyl, C 1 -C 10 dialkylaminoalkyl, (C 1 -C 10 alkyl)carbonyl, aryl(C 0 -C 6 alkyl)carbonyl, C 1 -C 10 alkenyl, C 1 -C 10 alkynyl ,C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O)R 17 , CONR 17 R 20 , SO 2 R 17 , or SO 2 NR 17 R 20 , provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-2 R 11 ;

›DETAILED DESCRIPTION OF THE INVENTION · 7 of 21

Y is selected from:

--COR 19 , --SO 3 H, --PO 3 H, tetrazolyl, --CONHNHSO 2 CF 3 , --CONHSO 2 R 17 , --CONHSO 2 NHR 17 , --NHCOCF 3 , --NHCONHSO 2 R 17 , --NHSO 2 R 17 , --OPO 3 H 2 , --OSO 3 H, --PO 3 H 2 , --SO 3 H, --SO 2 NHCOR 17 , --SO 2 NHCO 2 R 17 , ##STR21## R 16 is selected from: --N(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --NR 20 R 17 ;

R 17 is selected from:

R 18 is selected from:

--C(═O)--O--R 17 ,

--C(═O)--R 17 ,

--C(═O)--NH--R 17 ,

--SO 2 --R 17 , or

--SO 2 --NR 20 R 17 ;

R 19 is selected from hydroxy, C 1 -C 10 alkyloxy, C 3 -C 11 cycloalkyloxy, aryloxy, aryl(C 1 -C 6 alkoxy)-, C 3 -C 10 alkylcarbonyloxyalkyloxy, C 3 -C 10 alkoxycarbonyloxyalkyloxy, C 2 -C 10 alkoxycarbonylalkyloxy, C 5 -C 10 cycloalkylcarbonyloxyalkyloxy, C 5 -C 10 cycloalkoxycarbonyloxyalkyloxy, C 5 -C 10 cycloalkoxycarbonylalkyloxy, C 7 -C 11 aryloxycarbonylalkyloxy, C 8 -C 12 aryloxycarbonyloxyalkyloxy, C 8 -C 12 arylcarbonyloxyalkyloxy, C 5 -C 10 alkoxyalkylcarbonyloxyalkyloxy, C 5 -C 10 (5-alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C 10 -C 14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R 11 )(R 12 )N-(C 1 -C 10 alkoxy)-;

R 20 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

R 21 is selected from COOH or NR 6 2 ;

m is 0-4;

n is 0-4;

t is 0-4;

p is 0-2;

q is 0-2; and

r is 0-2;

with the following provisos:

(1) t, n, m and q are chosen such that the number of atoms connecting R 1 and Y is in the range of 10-14; and

(2) n and m are chosen such that the value of n plus m is greater than one unless U is --(CH 2 ) n Q(CH 2 ) m --.

7! Preferred compounds of the invention as described above are compounds of the Formula Ib: ##STR22## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof, wherein:

X 1 , X 2 , X 3 , and X 4 are independently selected from nitrogen or carbon provided that at least two of X 1 , X 2 , X 3 and X 4 are carbon;

R 1 is selected from: ##STR23## A and B are independently --CH 2 --, --O--, --N(R 2 )--, or --C(═O)--;

A 1 and B 1 are independently --CH 2 -- or --N(R 3 )--;

D is --N(R 2 )--, --O--, --S--, --C(═O)-- or --SO 2 --;

E--F is --C(R 4 ) ═C(R 5 )--, -N═C(R 4 )--, --C(R 4 )═N--, or --C(R 4 ) 2 C(R 5 ) 2 --;

J, K, L and M are independently selected from --C(R 4 )--, --C(R 5 )-- or --N--, provided that at least one of J, K, L and M is not --N--;

R 2 is selected from: H, C 1 -C 6 alkyl, (C 1 -C 6 alkyl)carbonyl, (C 1 -C 6 alkoxy)carbonyl, C 1 -C 6 alkylaminocarbonyl, C 3 -C 6 alkenyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, heteroaryl(C 1 -C 6 alkyl)carbonyl, heteroarylcarbonyl, aryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)carbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, aryl(C 1 -C 6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C 1 -C 6 alkyl)sulfonyl, aryloxycarbonyl, aryl(C 1 -C 6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo, CF 3 , and nitro;

R 3 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

U is selected from:

--(CH 2 ) n --,

--(CH 2 ) n (CR 7 ═CR 8 )(CH 2 ) m --

--(CH 2 ) t Q(CH 2 ) m --,

--(CH 2 ) n O(CH 2 ) m --,

--(CH 2 ) n N(R 6 )(CH 2 ) m --,

--(CH 2 ) n C(═O)(CH 2 ) m --, or

--(CH 2 ) n S(O) p (CH 2 ) m --;

wherein one of the methylene groups is optionally substituted with R 7 ;

Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl;

R 7 and R 8 are independently selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 0 -C 6 alkyl)-;

R 11 is selected from: H, halogen, CF 3 , CN, NO 2 , hydroxy, NR 2 R 3 , C 1 -C 4 alkyl substituted with 0-1 R 21 , C 1 -C 4 alkoxy substituted with 0-1 R 21 , aryl substituted with 0-1 R 21 aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 21 , (C 1 -C 4 alkoxy)carbonyl substituted with 0-1 R 21 , (C 1 -C 4 alkyl)carbonyl substituted with 0-1 R 21 , C 1 -C 4 alkylsulfonyl substituted with 0-1 R 21 , or C 1 -C 4 alkylaminosulfonyl substituted with 0-1 R 21 ;

W is --C(═O)--N(R 13 )--(C(R 12 ) 2 ) q --;

X is --C (R 12 )(R 14 )--C (R 12 )(R 15 )--;

›DETAILED DESCRIPTION OF THE INVENTION · 8 of 21

alternatively, W and X can be taken together to be ##STR24## R 12 is H or C 1 -C 6 alkyl; R 13 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkylmethyl, or aryl(C 1 -C 6 alkyl)-;

R 14 is selected from:

H, C 1 -C 6 alkylthioalkyl, aryl(C 1 -C 10 alkylthioalkyl)-, aryl(C 1 -C 10 alkoxyalkyl)-, C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl(C 0 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O)R 17 or CONR 17 R 20 , provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-1 R 16 or 0-2 R 11 ;

R 15 is selected from:

H, R 16 , C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 10 alkylaminoalkyl, C 1 -C 10 dialkylaminoalkyl, C 1 -C 10 alkylcarbonyl, aryl(C 0 -C 6 alkyl)carbonyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl ,C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O)R 17 , CONR 17 R 20 , SO 2 R 17 , or SO 2 NR 17 R 20 , provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-2 R 11 ;

Y is selected from: ##STR25## R 16 is selected from: --N(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 or

--N(R 20 )SO 2 --NR 20 R 17 ;

R 17 is selected from:

C 1 -C 10 alkyl, C 3 -C 11 cycloalkyl, aryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)aryl, heteroaryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)heteroaryl, biaryl(C 0 -C 6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C 1 -C 4 alkyl, C 1 -C 4 alkoxy, aryl, heteroaryl, halo,cyano, amino, CF 3 , and NO 2 ;

R 18 is selected from:

--C(═O)--O--R 17 ,

--C(═O)--R 17 ,

--C(═O)--NH--R 17 ,

--SO 2 --R 17 , or

--SO 2 --NR 20 R 17 ;

R 19 is selected from hydroxy, C 1 -C 10 alkyloxy, C 3 -C 11 cycloalkyloxy, C 6 -C 10 aryloxy, C 7 -C 11 aralkyloxy, C 3 -C 10 alkylcarbonyloxyalkyloxy, C 3 -C 10 alkoxycarbonyloxyalkyloxy, C 2 -C 10 alkoxycarbonylalkyloxy, C 5 -C 10 cycloalkylcarbonyloxyalkyloxy, C 5 -C 10 cycloalkoxycarbonyloxyalkyloxy, C 5 -C 10 cycloalkoxycarbonylalkyloxy, C 7 -C 11 aryloxycarbonylalkyloxy, C 8 -C 12 aryloxycarbonyloxyalkyloxy, C 8 -C 12 arylcarbonyloxyalkyloxy, C 5 -C 10 alkoxyalkylcarbonyloxyalkyloxy, C 5 -C 10 (5-alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C 10 -C 14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R 11 )(R 12 )N--(C 1 -C 10 alkoxy)-;

R 20 selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

R 21 is selected from COOH or NR 6 2 ;

m is 0-4;

n is 0-4;

t is 0-4;

p is 0-2;

q is 0-2; and

r is 0-2.

8! Further preferred compounds of the invention as described above are compounds of the Formula IIc or IId: ##STR26## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof, wherein:

X 1 and X 3 are independently selected from nitrogen or carbon;

R 1 is selected from: ##STR27## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH 2 , halogen, NO 2 , CN, CF 3 , C 1 -C 4 alkoxy, C 1 -C 6 alkyl, and C 3 -C 7 cycloalkyl;

U is --(CH 2 ) n --, --(CH 2 ) t Q(CH 2 ) m -- or --C(═O)(CH 2 ) n-1 --, wherein one of the methylene groups is optionally substituted with R 7 ;

Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyrdinylene, or 2,4-pyridinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl;

R 7 is selected from: C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl), heteroaryl, or heteroaryl(C 1 -C 6 alkyl);

R 9 is selected from: H, --SO 2 R 17 , --SO 2 NR 17 R 20 , C 1 -C 6 alkyl substituted with 0-1 R 15 or 0-1 R 21 , C 3 -C 7 cycloalkyl substituted with 0-1 R 15 or 0-1 R 21 , C 4 -C 11 cycloalkylalkyl substituted with 0-1 R 15 or 0-1 R 21 , aryl substituted with 0-1 R 15 or 0-2 R 1 l or 0-1 R 21 , or aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 ;

R 11 is selected from: H, halogen, CF 3 , CN, NO 2 , hydroxy, NR 2 R 3 , C 1 -C 4 alkyl substituted with 0-1 R 21 , C 1 -C 4 alkoxy substituted with 0-1 R 21 , aryl substituted with 0-1 R 21 , aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 21 (C 1 -C 4 alkoxy)carbonyl substituted with 0-1 R 21 (C 1 -C 4 alkyl)carbonyl substituted with 0-1 R 21 , C 1 -C 4 alkylsulfonyl substituted with 0-1 R 21 , or C 1 -C 4 alkylaminosulfonyl substituted with 0-1 R 21 ;

W is --C(═O)--N(R 13 )--;

X is --CH(R 14 )--CH(R 15 )--;

R 13 is H or CH 3 ;

R 14 is selected from:

R 15 is H or R 16 ;

Y is --COR 19 ;

R 16 is selected from:

--NH(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --N(R 20 )R 17 ;

R 17 is selected from:

R 19 is selected from:

hydroxy, C 1 -C 10 alkoxy,

methylcarbonyloxymethoxy-,

ethylcarbonyloxymethoxy-,

t-butylcarbonyloxymethoxy-,

cyclohexylcarbonyloxymethoxy-,

1-(methylcarbonyloxy)ethoxy-,

1-(ethylcarbonyloxy)ethoxy-,

1-(t-butylcarbonyloxy)ethoxy-,

1-(cyclohexylcarbonyloxy)ethoxy-,

i-propyloxycarbonyloxymethoxy-,

›DETAILED DESCRIPTION OF THE INVENTION · 9 of 21

t-butyloxycarbonyloxymethoxy-,

1-(i-propyloxycarbonyloxy)ethoxy-,

1-(cyclohexyloxycarbonyloxy)ethoxy-,

1-(t-butyloxycarbonyloxy)ethoxy-,

dimethylaminoethoxy-,

diethylaminoethoxy-,

(5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or

1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-;

R 20 is H or CH 3 ;

R 21 is selected from COOH or NR 6 2 ; and

m is 0 or 1;

n is 1-4; and

t is 0 or 1.

9! Still further preferred compounds of the above invention are compounds of the Formula IIc or IId: ##STR28## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof, wherein:

X 1 and X 3 are independently selected from nitrogen or carbon, provided that at least one of X 1 and X 3 is carbon;

R 1 is selected from: ##STR29## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH 2 , halogen, NO 2 , CN, CF 3 , C 1 -C 4 alkoxy, C 1 -C 6 alkyl and C 3 -C 7 cycloalkyl:

U is --(CH 2 ) n --, --(CH 2 ) t Q (CH 2 ) m -- or --C(═O)(CH 2 ) n-1 --, wherein one of the methylene groups is optionally substituted with R 7 ;

Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl;

R7 is selected from: C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl), heteroaryl, or heteroaryl(C 1 -C 6 alkyl);

R 9 is selected from: H, --SO 2 R 17 , --SO 2 NR 17 R 20 , C 1 -C 6 alkyl substituted with 0-1 R 15 or 0-1 R 21 , C 3 -C 7 cycloalkyl substituted with 0-1 R 15 or 0-1 R 21 , C 4 -C 11 cycloalkylalkyl substituted with 0-1 R 15 or 0-1 R 21 , aryl substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 , or aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 ;

W is --C(═O)--N(R 13 )--;

X is --CH(R 14 )--CH(R 15 )--;

R 13 is H or CH 3 ;

R 14 is selected from:

R 15 is H or R 16 ;

Y is --COR 19 ;

R 16 is selected from:

--N(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --NR 20 R 17 ;

R 17 is selected from:

R 19 is selected from:

hydroxy, C 1 -C 10 alkoxy,

methylcarbonyloxymethoxy-,

ethylcarbonyloxymethoxy-,

t-butylcarbonyloxymethoxy-,

cyclohexylcarbonyloxymethoxy-,

1-(methylcarbonyloxy)ethoxy-,

1-(ethylcarbonyloxy)ethoxy-,

1-(t-butylcarbonyloxy)ethoxy-,

1-(cyclohexylcarbonyloxy)ethoxy-,

i-propyloxycarbonyloxymethoxy-,

t-butyloxycarbonyloxymethoxy-,

1-(i-propyloxycarbonyloxy)ethoxy-,

1-(cyclohexyloxycarbonyloxy)ethoxy-,

1-(t-butyloxycarbonyloxy)ethoxy-,

dimethylaminoethoxy-,

diethylaminoethoxy-,

(5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or

1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-;

R 20 is H or CH 3 ;

R 21 is selected from COOH or NR 6 2 ; and

m is 0 or 1;

n is 1-4; and

t is 0 or 1.

10! Specifically preferred compounds of the invention as described above are compounds of Formula Ib, including enantiomeric or diasteriomeric forms thereof, or mixtures of enantiomeric or diasteriomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof, selected from the group consisting of:

3- 3- 3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazolin-2-ylamino)propyl!-indazol-6-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1-methyl-3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

›DETAILED DESCRIPTION OF THE INVENTION · 10 of 21

3- 1-methyl-3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(tetrahydropyrimid-2-ylamino)propyl!-indazol-6-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 3- 3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1-methyl-3- 3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 3- 3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1-methyl-3- 3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1-methyl-3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1-methyl-3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid,

3- 3- 3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzyloxycarbonylamino)propionic acid,

3- 1-methyl-3- 3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzenesulfonylamino)propionic acid,

3- 1-methyl-3- 3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid,

3- 3- 3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(3,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid,

3- 1-methyl-3- 3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid,

3- 3- 3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid, and

3- 1-methyl-3- 3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(4-phenylbenzenesulfonylamino)propionic acid.

›DETAILED DESCRIPTION OF THE INVENTION · 11 of 21

11! Also specifically preferred are ester prodrugs of the specifically preferred compounds of Formula Ib, said esters being chosen from the group consisting of:

methyl,

ethyl,

isopropyl,

n-butyl,

isobutyl,

benzyl,

methylcarbonyloxymethyl,

ethylcarbonyloxymethyl,

tert-butylcarbonyloxymethyl,

cyclohexylcarbonyloxymethyl,

tert-butyloxycarbonyloxymethyl,

dimethylaminoethyl, and

diethylaminoethyl,

pyrroldinoethyl, and

trimethylanimonioethyl.

12! Yet another aspect of the present invention comprises compounds of Formula Ic: ##STR30## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms, thereof wherein:

X 1 , X 2 , X 3 , and X 4 are independently selected from nitrogen or carbon provided that at least two of X 1 , X 2 , X 3 and X 4 are carbon;

R 1 is selected from: ##STR31## A and B are independently --CH 2 --, --O--, --N(R 2 )--, or --C(═O)--;

A 1 and B 1 are independently --CH 2 -- or --N(R 3 )--;

D is --N(R 2 )--, --O--, --S--, --C(═O)-- or --SO 2 --;

E--F is --C(R 4 )═C(R 5 )--, --N═C(R 4 )--, --C(R 4 )═N--, or --C(R 4 ) 2 C(R 5 ) 2 --;

J, K, L and M are independently selected from --C(R 4 )--, --C(R 5 )-- or --N--, provided that at least one of J, K, L and M is not --N--;

R 2 is selected from: H, C 1 -C 6 alkyl, (C 1 -C 6 alkyl)carbonyl, (C 1 -C 6 alkoxy)carbonyl; (C 1 -C 6 alkyl)aminocarbonyl, C 3 -C 6 alkenyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, heteroaryl(C 1 -C 6 alkyl)carbonyl, heteroarylcarbonyl, aryl C 1 -C 6 alkyl, (C 1 -C 6 alkyl)carbonyl, or arylcarbonyl, C 1 -C 6 alkylsulfonyl, arylsulfonyl aryl(C 1 -C 6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C 1 -C 6 alkyl)sulfonyl, aryloxycarbonyl, or aryl(C 1 -C 6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo, CF 3 , and nitro;

R 3 is selected from: H, C 1 -C 6 alkyl, C 3-C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

U is selected from:

--(CH 2 ) n --,

--(CH 2 ) n (CR 7 ═CR 8 )(CH 2 ) m --

--(CH 2 ) n (C.tbd.C)(CH 2 ) m --

--(CH 2 ) t Q(CH 2 ) m --

--(CH 2 ) n O(CH 2 ) m --,

--(CH 2 ) n N(R 6 )(CH 2 ) m --,

--(CH 2 ) n C(═O)(CH 2 ) m --,

--(CH 2 ) n (C═O)N(R 6 )(CH 2 ) m --

--(CH 2 ) n N(R 6 )(C═O)(CH 2 ) m --, or

--(CH 2 ) n S(O) p (CH 2 ) m --;

wherein one of the methylene groups is optionally substituted with R 7 ;

Q is selected from 1,2-cycloalkylene, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, 2,4-pyridinylene, or 3,4-pyridazinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl;

R 7 and R 8 are independently selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 0 -C 6 alkyl)-;

W is selected from:

--(C(R 12 ) 2 ) q C(═O)N(R 13 )--, or

--C(═O)--N(R 13 )--(C(R 12 ) 2 ) q --;

X is --C(R 12 )(R 14 )--C(R 12 )(R 15 )--; or

alternatively, W and X can be taken together to be ##STR32## R 12 is selected from: H, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl, C 4 -C 10 cycloalkylalkyl, (C 1 -C 4 alkyl)carbonyl, aryl, or aryl(C 1 -C 6 alkyl)-;

R 13 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkylmethyl, or aryl(C 1 -C 6 alkyl)

R 14 is selected from:

H, C 1 -C 6 alkylthio(C 1 -C 6 alkyl)-, aryl(C 1 -C 10 alkylthioalkyl)-, aryl(C 1 -C 10 alkoxyalkyl)-, C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O)R 17 , or CONR 17 R 20 , provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-1 R 16 or 0-2 R 11 ;

R 15 is selected from:

›DETAILED DESCRIPTION OF THE INVENTION · 12 of 21

Y is selected from:

--COR 19 , --SO 3 H, --PO 3 H, tetrazolyl, --CONHNHSO 2 CF 3 , --CONHSO 2 R 17 , --CONHSO 2 NHR 17 , --NHCOCF 3 , --NHCONHSO 2 R 17 , --NHSO 2 R 17 , --OPO 3 H 2 , --OSO 3 H, --PO 3 H 2 , --SO 3 H, --SO 2 NHCOR 17 , --SO 2 NHCO 2 R 17 , ##STR33## R 16 is selected from: --N(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --NR 20 R 17 ;

R 17 is selected from:

R 18 is selected from:

--C(═O)--O--R 17 ,

--C(═O)--R 17 ,

--C(═O)--NH--R 17 ,

--SO 2 --R 17 , or

--SO 2 --NR 20 R 17 ;

R 20 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

R 21 is selected from COOH or NR 6 2 ;

m is 0-4;

n is 0-4;

p is 0-2;

q is 0-2; and

r is 0-2;

with the following provisos:

(1) t, n, m and q are chosen such that the number of atoms connecting R 1 and Y is in the range of 10-14; and

(2) n and m are chosen such that the value of n plus m is greater than one unless U is --(CH 2 ) t Q(CH 2 ) m --.

13! Preferred compounds of the invention as described above are compounds of the Formula Ic: ##STR34## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof wherein:

X 1 , X 2 , X 3 , and X 4 are independently selected from nitrogen or carbon provided that at least two of X 1 , X 2 , X 3 and X 4 are carbon;

R 1 is selected from: ##STR35## A and B are independently --CH 2 --, --O--, --N(R 2 )--, or --C(═O)--;

A 1 and B 1 are independently --CH 2 -- or --N(R 3 )--;

D is --N(R 2 )--, --O--, --S--, --C(═O)-- or --SO 2 --;

E-F is --C(R 4 )═C(R 5 )--, --N═C(R 4 )--, --C(R 4 )═N--, or --C(R 4 ) 2 C(R 5 ) 2 --;

J, K, L and M are independently selected from: --C(R 4 )--, --C(R 5 )-- or --N--, provided that at least one of J, K, L and M is not --N--;

R 2 is selected from: H, C 1 -C 6 alkyl, (C 1 -C 6 alkyl)carbonyl, (C 1 -C 6 alkoxy)carbonyl, C 1 -C 6 alkylaminocarbonyl, C 3 -C 6 alkenyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, heteroaryl(C 1 -C 6 alkyl)carbonyl, heteroarylcarbonyl, aryl(C 1 -C 6 alkyl)-, (C 1 -C 6 alkyl)carbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, aryl(C 1 -C 6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C 1 -C 6 alkyl)sulfonyl, aryloxycarbonyl, aryl(C 1 -C 6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy, halo, CF 3 , and nitro;

R 3 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

U is selected from:

--(CH 2 ) n --,

--(CH 2 ) n (CR 7 ═CR 8 )(CH 2 ) m --

--(CH 2 ) t Q(CH 2 ) m --,

--(CH 2 ) n O(CH 2 ) m --,

--(CH 2 ) n N(R 6 )(CH 2 ) m --,

--(CH 2 ) n C(═O)(CH 2 ) m --, or

--(CH 2 ) n S(O) p (CH 2 ) m --;

wherein one of the methylene groups is optionally substituted with R 7 ;

Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl;

R 7 and R 8 are independently selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cylcloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 0 -C 6 alkyl)-;

R 11 is selected from: H, halogen, CF 3 , CN, NO 2 , hydroxy, NR 2 R 3 , C 1 -C 4 alkyl substituted with 0-1 R 21 , C 1 -C 4 alkoxy substituted with 0-1 R 21 , aryl substituted with 0-1 R 21 , aryl(C 1 -C 6 alkyl)- substituted with 0-1 R 21 , (C 1 -C 4 alkoxy)carbonyl substituted with 0-1 R 21 , (C 1 -C 4 alkyl)carbonyl substituted with 0-1 R 21 , C 1 -C 4 alkylsulfonyl substituted with 0-1 R 21 , or C 1 -C 4 alkylaminosulfonyl substituted with 0-1 R 21 ;

W is --C(═O)--N(R 13 )--(C(R 12 ) 2 ) q --;

X is --C(R 12 )(R 14 )--C(R 12 )(R 15 )--; alternatively, W and X can be taken together to be ##STR36## R 12 is H or C 1 -C 6 alkyl; R 13 is selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkylmethyl, or aryl(C 1 -C 6 alkyl)-;

›DETAILED DESCRIPTION OF THE INVENTION · 13 of 21

R 14 is selected from:

H, C 1 -C 6 alkylthioalkyl, aryl(C 1 -C 10 alkylthioalkyl)-, aryl(C 1 -C 10 alkoxyalkyl)-, C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O)R 17 , or CONR 17 R 20 , provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-1 R 16 or 0-2 R 11 ;

R 15 is selected from:

H, R 16 , C 1 -C 10 alkyl, C 1 -C 10 alkoxyalkyl, C 1 -C 10 alkylaminoalkyl, C 1 -C 10 dialkylaminoalkyl, C 1 -C 10 alkylcarbonyl, aryl(C 1 -C 6 alkyl)carbonyl, C 2 -C 10 alkenyl, C 2 -C 10 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, heteroaryl(C 1 -C 6 alkyl)-, aryl, heteroaryl, CO 2 R 17 , C(═O)R 17 , CONR 17 R 20 , SO 2 R 17 , or SO 2 NR 17 R 20 , provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-2 R 11 ;

Y is selected from: ##STR37## R 16 is selected from: --N(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --NR 20 R 17 ;

R 17 is selected from:

R 18 is selected from:

--C(═O)--O--R 17 ,

--C(═O)--R 17 ,

--C(═O)--NH--R 17 ,

--SO 2 --R 17 , or

--SO 2 --NR 20 R 17 ;

R 19 is selected from: hydroxy, C 1 -C 10 alkyloxy, C 3 -C 11 cycloalkyloxy, C 6 -C 10 aryloxy, C 7 -C 11 aralkyloxy, C 3 -C 10 alkylcarbonyloxyalkyloxy, C 3 -C 10 alkoxycarbonyloxyalkyloxy, C 2 -C 10 alkoxycarbonylalkyloxy, C 5 -C 10 cycloalkylcarbonyloxyalkyloxy, C 5 -C 10 cycloalkoxycarbonyloxyalkyloxy, C 5 -C 10 cycloalkoxycarbonylalkyloxy, C 7 -C 11 aryloxycarbonylalkyloxy, C 8 -C 12 aryloxycarbonyloxyalkyloxy, C 8 -C 12 arylcarbonyloxyalkyloxy, C 5 -C 10 alkoxyalkylcarbonyloxyalkyloxy, C 5 -C 10 (5-alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C 10 -C 14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R 11 )(R 12 )N--(C 1 -C 10 alkoxy)-;

R 20 selected from: H, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl(C 1 -C 6 alkyl)-, or heteroaryl(C 1 -C 6 alkyl)-;

R 21 is selected from COOH or NR 6 2 ;

m is 0-4;

n is 0-4;

t is 0-4;

p is 0-2;

q is 0-2; and

r is 0-2.

14! Further preferred compounds of the invention as described above are compounds of the Formula IIe or IIf: ##STR38## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof, wherein:

R 1 is selected from: ##STR39## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH 2 , halogen, NO 2 , CN, CF 3 , C 1 -C 4 alkoxy, C 1 -C 6 alkyl, and C 3 -C 7 cycloalkyl;

U is --(CH 2 ) n --, --(CH 2 ) t Q(CH 2 ) m -- or --C(═O)(CH 2 ) n-1 --, wherein one of the methylene groups is optionally substituted with R 7 ;

Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyrdinylene, or 2,4-pyridinylene;

R 6 is selected from: H, C 1 -C 4 alkyl, or benzyl;

R7 is selected from: C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl), heteroaryl, or heteroaryl(C 1 -C 6 alkyl);

R 9 is selected from: H, --SO 2 R 17 , --SO 2 NR 17 R 20 , C 1 -C 6 alkyl substituted with 0-1 R 15 or 0-1 R 21 , C 3 -C 7 cycloalkyl substituted with 0-1 R 15 or 0-1 R 21 , C 4 -C 11 cycloalkylalkyl substituted with 0-1 R 15 or 0-1 R 21 aryl substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 , or aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 ;

R 11 is selected from H, halogen, CF 3 , CN, NO 2 , hydroxy, NR 2 R 3 , C 1 -C 4 alkyl substituted with 0-1 R 21 , C 1 -C 4 alkoxy substituted with 0-1 R 21 , aryl substituted with 0-1 R 21 1 aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 21 , (C 1 -C 4 alkoxy)carbonyl substituted with 0-1 R 21 , (C 1 -C 4 alkyl)carbonyl substituted with 0-1 R 21 , C 1 -C 4 alkylsulfonyl substituted with 0-1 R 21 , or C 1 -C 4 alkylaminosulfonyl substituted with 0-1 R 21 ;

W is --C(═O)--N(R 13 )--;

X is --CH(R 14 )--CH(R 15 )--;

R 13 is H or CH 3 ;

R 14 is selected from:

R 15 is H or R 16 ;

Y is --COR 19 ;

R 16 is selected from:

--NH(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --N(R 20 )R 17 ;

R 17 is selected from:

R 19 is selected from:

hydroxy, C 1 -C 10 alkoxy,

methylcarbonyloxymethoxy-,

ethylcarbonyloxymethoxy-,

t-butylcarbonyloxymethoxy-,

cyclohexylcarbonyloxymethoxy-,

1-(methylcarbonyloxy)ethoxy-,

1-(ethylcarbonyloxy)ethoxy-,

1-(t-butylcarbonyloxy)ethoxy-,

1-(cyclohexylcarbonyloxy)ethoxy-,

i-propyloxycarbonyloxymethoxy-,

t-butyloxycarbonyloxymethoxy-,

1-(i-propyloxycarbonyloxy)ethoxy-,

1-(cyclohexyloxycarbonyloxy)ethoxy-,

1-(t-butyloxycarbonyloxy)ethoxy-,

dimethylaminoethoxy-,

diethylaminoethoxy-,

(5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

›DETAILED DESCRIPTION OF THE INVENTION · 14 of 21

(1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or

1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-;

R 20 is H or CH 3 ;

R 21 is selected from COOH or NR 6 2 ; and

m is 0 or 1;

n is 1-4; and

t is 0 or 1.

15! Still further preferred compounds of the above described are compounds of the Formula IIe or IIf: ##STR40## including stereoisomeric forms thereof, or mixtures of stereoisomeric forms thereof, or pharmaceutically acceptable salt or prodrug forms thereof, wherein: R 1 is selected from: ##STR41## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH 2 , halogen, NO 2 , CN, CF 3 , C 1 -C 4 alkoxy, C 1 -C 6 alkyl, and C 3 -C 7 cycloalkyl:

U is --(CH 2 ) n --, --(CH 2 ) t Q(CH 2 ) m -- or --C(═O)(CH 2 ) n-1 --, wherein one of the methylene groups is optionally substituted with R 7 ;

Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene;

R 6 selected from: H, C 1 -C 4 alkyl, or benzyl;

R7 is selected from C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 4 -C 11 cycloalkylalkyl, aryl, aryl(C 1 -C 6 alkyl), heteroaryl, or heteroaryl(C 1 -C 6 alkyl);

R 9 is selected from: H, --SO 2 R 17 , --SO 2 NR 17 R 20 , C 1 -C 6 alkyl substituted with 0-1 R 15 or 0-1 R 21 , C 3 -C 7 cycloalkyl substituted with 0-1 R 15 or 0-1 R 21 , C 4 -C 11 cycloalkylalkyl substituted with 0-1 R 15 or 0-1 R 21 , aryl substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 , or aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 15 or 0-2 R 11 or 0-1 R 21 ;

R 11 is selected from H, halogen, CF 3 CN, NO 2 , hydroxy, NR 2 R 3 C 1 -C 4 alkyl substituted with 0-1 R 21 C 1 -C 4 alkoxy substituted with 0-1 R 21 , aryl substituted with 0-1 R 21 , aryl(C 1 -C 6 alkyl)-substituted with 0-1 R 21 (C 1 -C 4 alkoxy)carbonyl substituted with 0-1 R 21 (C 1 -C 4 alkyl)carbonyl substituted with 0-1 R 21 , C 1 -C 4 alkylsulfonyl substituted with 0-1 R 21 , or C 1 -C 4 alkylaminosulfonyl substituted with 0-1 R 21 ;W is --C(═O)--N(R 13 )--;

W is --C(═O)--N(R 13 )--;

X is --CH(R 14 )--CH(R 15 )

R 13 is H or CH 3 ;

R 14 is selected from:

R 15 is H or R 16 ;

Y is --COR 19 ;

R 16 is selected from:.

--NH(R 20 )--C(═O)--O--R 17 ,

--N(R 20 )--C(═O)--R 17 ,

--N(R 20 )--C(═O)--NH--R 17 ,

--N(R 20 )SO 2 --R 17 , or

--N(R 20 )SO 2 --NR 20 R 17 ;

R 17 is selected from:

R 19 is selected from:

hydroxy, C 1 -C 10 alkoxy,

methylcarbonyloxymethoxy-,

ethylcarbonyloxymethoxy-,

t-butylcarbonyloxymethoxy-,

cyclohexylcarbonyloxymethoxy-,

1-(methylcarbonyloxy)ethoxy-,

1-(ethylcarbonyloxy)ethoxy-,

1-(t-butylcarbonyloxy)ethoxy-,

1-(cyclohexylcarbonyloxy)ethoxy-,

i-propyloxycarbonyloxymethoxy-,

t-butyloxycarbonyloxymethoxy-,

1-(i-propyloxycarbonyloxy)ethoxy-,

1-(cyclohexyloxycarbonyloxy)ethoxy-,

1-(t-butyloxycarbonyloxy)ethoxy-,

dimethylaminoethoxy-,

diethylaminoethoxy-,

(5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-,

(1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or

1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-;

R 20 is H or CH 3 ;

R 21 is selected from COOH or NR 6 2 ; and

m is 0 or 1;

n is 1-4; and

t is 0 or 1.

In the present invention it has been discovered that the compounds of Formula Ia, Ib or Ic above are useful as inhibitors of cell-matrix and cell-cell adhesion processes. The present invention includes novel compounds of Formula Ia, Ib or Ic and methods for using such compounds for the prevention or treatment of diseases resulting from abnormal cell adhesion to the extracellular matrix which comprises administering to a host in need of such treatment a therapeutically effective amount of such compound of Formula Ia, Ib or Ic.

In the present invention it has also been discovered that the compounds of Formula Ia, Ib or Ic above are useful as inhibitors of α v β 3 . The compounds of the present invention inhibit the binding of vitronectin to α v β 3 and inhibit cell adhesion.

The present invention also provides pharmaceutical compositions comprising a compound of Formula Ia, Ib or Ic and a pharmaceutically acceptable carrier.

The compounds of Formula Ia, Ib or Ic of the present invention are useful for the treatment (including prevention) of angiogenic disorders, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula Ia, Ib or Ic described above. The term "angiogenic disorders" as used herein includes conditions involving abnormal neovascularization, such as tumor metastasis and ocular neovascularization, including, for example, diabetic retinopathy, neovascular glaucoma, age-related macular degeneration, and retinal vein occlusion.

The compounds of Formula Ia, Ib or Ic of the present invention are also useful for the treatment (including prevention) of thromboembolic disorders, comprising administering to a mammal in need of such treatment a therapeutically effective amount of a compound of Formula Ia, Ib or Ic described above. The term "thromboembolic disorders" as used herein includes conditions involving platelet activation and aggregation, such as arterial or venous cardiovascular or cerebrovascular thromboembolic disorders, including, for example, thrombosis, unstable angina, first or recurrent myocardial infarction, ischemic sudden death, transient ischemic attack, stroke, atherosclerosis, venous thrombosis, deep vein thrombosis, thrombophlebitis, arterial embolism, coronary and cerebral arterial thrombosis, myocardial infarction, cerebral embolisms, kidney embolisms, pulmonary embolisms, or such disorders associated with diabetes.

›DETAILED DESCRIPTION OF THE INVENTION · 15 of 21

The compounds of Formula Ia, Ib or Ic of the present invention may also be useful for the treatment or prevention of other diseases which involve cell adhesion processes, including, but not limited to, inflammation, bone degradation, restenosis, rheumatoid arthritis, asthma, allergies, adult respiratory distress syndrome, graft versus host disease, organ transplantation rejection, septic shock, psoriasis, eczema, contact dermatitis, osteoporosis, osteoarthritis, atherosclerosis, inflammatory bowel disease and other autoimmune diseases. The compounds of Formula Ia, Ib or Ic of the present invention may also be useful for wound healing.

The compounds of the present invention may be used for other ex vivo applications to prevent cellular adhesion in biological samples.

The compounds of the present invention can also be administered in combination with one or more additional therapeutic agents selected from: anti-coagulant or coagulation inhibitory agents, such as heparin or warfarin; anti-platelet or platelet inhibitory agents, such as aspirin, piroxicam, or ticlopidine; thrombin inhibitors such as boropeptides, hirudin or argatroban; or thrombolytic or fibrinolytic agents, such as plasminogen activators, anistreplase, urokinase, or streptokinase.

The compounds of Formula Ia, Ib or Ic of the present invention can be administered in combination with one or more of the foregoing additional therapeutic agents, thereby to reduce the doses of each drug required to achieve the desired therapeutic effect. Thus, the combination treatment of the present invention permits the use of lower doses of each component, with reduced adverse, toxic effects of each component. A lower dosage minimizes the potential of side effects of the compounds, thereby providing an increased margin of safety relative to the margin of safety for each component when used as a single agent. Such combination therapies may be employed to achieve synergistic or additive therapeutic effects for the treatment of thromboembolic or other disorders.

By "therapeutically effective amount" is meant an amount of a compound of Formula Ia, Ib or Ic that when administered alone or in combination with an additional therapeutic agent to a cell or mammal is effective to prevent or ameliorate the disease condition or the progression of the disease.

By "administered in combination" or "combination therapy" it is meant that the compound of Formula Ia, Ib or Ic and one or more additional therapeutic agents are administered concurrently to the mammal being treated. When administered in combination each component may be administered at the same time or sequentially in any order at different points in time. Thus, each component may be administered separately but sufficiently closely in time so as to provide the desired therapeutic effect.

The term anti-coagulant agents (or coagulation inhibitory agents), as used herein, denotes agents that inhibit blood coagulation. Such agents include warfarin sodium crystalline clathrate and heparin.

The term anti-platelet agents (or platelet inhibitory agents), as used herein, denotes agents that inhibit platelet function such as by inhibiting the aggregation, adhesion or granular secretion of platelets. Such agents include the various known non-steroidal anti-inflammatory drugs (NSAIDS) such as aspirin, ibuprofen, naproxen, sulindac, indomethacin, mefenamate, droxicam, diclofenac, sulfinpyrazone, and piroxicam, including pharmaceutically acceptable salts or prodrugs thereof. Other suitable anti-platelet agents include ticlopidine, including pharmaceutically acceptable salts or prodrugs thereof. Ticlopidine is also a preferred compound since it is known to be gentle on the gastrointestinal tract in use. Still other suitable platelet inhibitory agents include thromboxane-A 2 -receptor antagonists and thromboxane-A 2 -synthetase inhibitors, as well as pharmaceutically acceptable salts or prodrugs thereof.

The phrase thrombin inhibitors (or anti-thrombin agents), as used herein, denotes inhibitors of the serine protease thrombin. By inhibiting thrombin, various thrombin-mediated processes, such as thrombin-mediated platelet activation (that is, for example, the aggregation of platelets, and/or the granular secretion of plasminogen activator inhibitor-1 and/or serotonin) and/or fibrin formation are disrupted. Such inhibitors include boroarginine derivatives and boropeptides, hirudin and argatroban, including pharmaceutically acceptable salts and prodrugs thereof. Boroarginine derivatives and boropeptides include N-acetyl and peptide derivatives of boronic acid, such as C-terminal α-aminoboronic acid derivatives of lysine, ornithine, arginine, homoarginine and corresponding isothiouronium analogs thereof. The term hirudin, as used herein, includes suitable derivatives or analogs of hirudin, referred to herein as hirulogs, such as disulfatohirudin. Boropeptide thrombin inhibitors include compounds described in Kettner et al., U.S. Pat. No. 5,187,157 and European Patent Application Publication Number 293 881 A2, the disclosures of which are hereby incorporated herein by reference. Other suitable boroarginine derivatives and boropeptide thrombin inhibitors include those disclosed in PCT Application Publication Number 92/07869 and European Patent Application Publication Number 471 651 A2, the disclosures of which are hereby incorporated herein by reference, in their entirety.

The phrase thrombolytics (or fibrinolytic) agents (or thrombolytics or fibrinolytics), as used herein, denotes agents that lyse blood clots (thrombi). Such agents include tissue plasminogen activator, anistreplase, urokinase, retivase or streptokinase, including pharmaceutically acceptable salts or prodrugs thereof. Tissue plasminogen activator (tPA) is commercially available from Genentech Inc., South San Francisco, Calif. The term anistreplase, as used herein, refers to anisoylated plasminogen streptokinase activator complex, as described, for example, in European Patent Application No. 028,489, the disclosures of which are hereby incorporated herein by reference herein, in their entirety. The term urokinase, as used herein, is intended to denote both dual and single chain urokinase, the latter also being referred to herein as prourokinase.

›DETAILED DESCRIPTION OF THE INVENTION · 16 of 21

The compounds of the present invention are also useful as standard or reference compounds, for example as a quality standard or control, in tests or assays involving the binding of vitronectin or fibrinogen to α v β 3 . Such compounds may be provided in a commercial kit, for example, for use in pharmaceutical research involving α v β 3 . The compounds of the present invention may also be used in diagnostic assays involving α v β 3 .

The compounds herein described may have asymmetric centers. Unless otherwise indicated, all chiral, diastereomeric and racemic forms are included in the present invention. Many geometric isomers of olefins, C═N double bonds, and the like can also be present in the compounds described herein, and all such stable isomers are contemplated in the present invention. It will be appreciated that compounds of the present invention that contain asymmetrically substituted carbon atoms may be isolated in optically active or racemic forms. It is well known in the art how to prepare optically active forms, such as by resolution of racemic forms or by synthesis, from optically active starting materials. All chiral, diastereomeric, racemic forms and all geometric isomeric forms of a structure are intended, unless the specific stereochemistry or isomer form is specifically indicated.

When any variable (for example but not limited to, R 2 , R 4 , R 6 , R 7 , R 8 , R 12 ,and R 14 , n, etc.) occurs more than one time in any constituent or in any formula, its definition on each occurrence is independent of its definition at every other occurrence. Thus, for example, if a group is shown to be substituted with 0-3 R 4 , then said group may optionally be substituted with up to three R 4 and R 4 at each occurrence is selected independently from the defined list of possible R 4 . Also, by way of example, for the group --N(R 5a ) 2 , each of the two R 5a substituents on N is independently selected from the defined list of possible R 5a . Similarly, by way of example, for the group --C(R 7 ) 2 --, each of the two R 7 substituents on C is independently selected from the defined list of possible R 7 .

When a bond to a substituent is shown to cross the bond connecting two atoms in a ring, then such substituent may be bonded to any atom on the ring. When a bond joining a substituent to another group is not specifically shown or the atom in such other group to which the bond joins is not specifically shown, then such substituent may form a bond with any atom on such other group.

When a substituent is listed without indicating the atom via which such substituent is bonded to the rest of the compound of Formula Ia, Ib or Ic, then such substituent may be bonded via any atom in such substituent. For example, when the substituent is piperazinyl, piperidinyl, or tetrazolyl, unless specified otherwise, said piperazinyl, piperidinyl, tetrazolyl group may be bonded to the rest of the compound of Formula Ia, Ib or Ic via any atom in such piperazinyl, piperidinyl, tetrazolyl group.

Combinations of substituents and/or variables are permissible only if such combinations result in stable compounds. By stable compound or stable structure it is meant herein a compound that is sufficiently robust to survive isolation to a useful degree of purity from a reaction mixture, and formulation into an efficacious therapeutic agent.

The term "substituted", as used herein, means that any one or more hydrogen on the designated atom is replaced with a selection from the indicated group, provided that the designated atom's normal valency is not exceeded, and that the substitution results in a stable compound. When a substitent is keto (i.e., ═O), then 2 hydrogens on the atom are replaced.

As used herein, "alkyl" is intended to include both branched and straight-chain saturated aliphatic hydrocarbon groups having the specified number of carbon atoms (for example, "C 0 -C 10 " denotes alkyl having 0 to 10 carbon atoms; C 0 denotes a direct bond between the groups linked by the C 0 group; also by way of example, "C 1 to C 4 " denotes methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-methylpropyl, 1-methylpropyl, 1,1-dimethyl ethyl); "haloalkyl" is intended to include both branched and straight-chain saturated aliphatic hydrocarbon groups having the specified number of carbon atoms, substituted with 1 or more halogen (for example --C v F w where v=1 to 3 and w=1 to (2v+1)); "alkoxy" represents an alkyl group of indicated number of carbon atoms attached through an oxygen bridge; "cycloalkyl" is intended to include saturated ring groups, including mono-,bi- or poly-cyclic ring systems, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and adamantyl; and "biycloalkyl" is intended to include saturated bicyclic ring groups such as 3.3.0!bicyclooctane, 4.3.0!bicyclononane, 4.4.0!bicyclodecane (decalin), 2.2.2!bicyclooctane, and so forth. "Alkenyl" is intended to include hydrocarbon chains of either a straight or branched configuration and one or more unsaturated carbon-carbon bonds which may occur in any stable point along the chain, such as ethenyl, propenyl and the like; and "alkynyl" is intended to include hydrocarbon chains of either a straight or branched configuration and one or more triple carbon-carbon bonds which may occur in any stable point along the chain, such as ethynyl, propynyl and the like.

The terms "alkylene", "alkenylene", "phenylene", and the like, refer to alkyl, alkenyl, and phenyl groups, respectively, which are connected by two bonds to the rest of the structure of Formula Ia, Ib or Ic. Such "alkylene", "alkenylene", "phenylene", and the like, may alternatively and equivalently be denoted herein as "-(alkyl)-", "-(alkyenyl)-" and "-(phenyl)-", and the like.

"Halo" or "halogen" as used herein refers to fluoro, chloro, bromo and iodo; and "counterion" is used to represent a small, negatively charged species such as chloride, bromide, hydroxide, acetate, sulfate and the like.

As used herein, "aryl" or "aromatic residue" is intended to mean phenyl or naphthyl; the term "arylalkyl" represents an aryl group attached through an alkyl bridge.

›DETAILED DESCRIPTION OF THE INVENTION · 17 of 21

As used herein, "carbocycle" or "carbocyclic residue" is intended to mean any stable 3- to 7-membered monocyclic or bicyclic or 7- to 14-membered bicyclic or tricyclic or an up to 26-membered polycyclic carbon ring, any of which may be saturated, partially unsaturated, or aromatic. Examples of such carbocyles include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, indanyl, adamantyl, or tetrahydronaphthyl (tetralin).

As used herein, the term "heterocycle" or "heterocyclic" is intended to mean a stable 5- to 7-membered monocyclic or bicyclic or 7- to 10-membered bicyclic heterocyclic ring which may be saturated, partially unsaturated, or aromatic, and which consists of carbon atoms and from 1 to 4 heteroatoms independently selected from the group consisting of N, O and S and wherein the nitrogen and sulfur heteroatoms may optionally be oxidized, and the nitrogen may optionally be quaternized, and including any bicyclic group in which any of the above-defined heterocyclic rings is fused to a benzene ring. The heterocyclic ring may be attached to its pendant group at any heteroatom or carbon atom which results in a stable structure. The heterocyclic rings described herein may be substituted on carbon or on a nitrogen atom if the resulting compound is stable. Examples of such heterocycles include, but are not limited to, pyridyl (pyridinyl), pyrimidinyl, furanyl (furyl), thiazolyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, tetrazolyl, benzofuranyl, benzothiophenyl, indolyl, indolenyl, isoxazolinyl, isoxazolyl, quinolinyl, isoquinolinyl, benzimidazolyl, piperidinyl, 4-piperidonyl, pyrrolidinyl, 2-pyrrolidonyl, pyrrolinyl, tetrahydrofuranyl, tetrahydroquinolinyl, tetrahydroisoquinolinyl, decahydroquinolinyl or octahydroisoquinolinyl, azocinyl, triazinyl, 6H-1,2,5-thiadiazinyl, 2H,6H-1,5,2-dithiazinyl, thianthrenyl, pyranyl, isobenzofuranyl, chromenyl, xanthenyl, phenoxathiinyl, 2H-pyrrolyl, pyrrolyl, imidazolyl, pyrazolyl, isothiazolyl, isoxazolinyl, isoxazolyl, oxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, indolizinyl, isoindolyl, 3H-indolyl, indolyl, 1H-indazolyl, purinyl, 4H-quinolizinyl, isoquinolinyl, quinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, pteridinyl, 4aH-carbazole, carbazole, β-carbolinyl, phenanthridinyl, acridinyl, perimidinyl, phenanthrolinyl, phenazinyl, phenarsazinyl, phenothiazinyl, furazanyl, phenoxazinyl, isochromanyl, chromanyl, pyrrolidinyl, pyrrolinyl, imidazolidinyl, imidazolinyl, pyrazolidinyl, pyrazolinyl, piperidinyl, piperazinyl, indolinyl, isoindolinyl, quinuclidinyl, morpholinyl or oxazolidinyl. Also included are fused ring and spiro compounds containing, for example, the above heterocycles.

As used herein, the term "heteroaryl" refers to aromatic heterocyclic groups. Such heteroaryl groups are preferably 5-6 membered monocyclic groups or 8-10 membered fused bicyclic groups. Examples of such heteroaryl groups include, but are not limited to pyridyl (pyridinyl), pyrimidinyl, furanyl (furyl), thiazolyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, indolyl, isoxazolyl, oxazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothienyl, benzimidazolyl, quinolinyl, or isoquinolinyl.

As used herein, "pharmaceutically acceptable salts" refer to derivatives of the disclosed compounds wherein the parent compound of Formula Ia, Ib or Ic is modified by making acid or base salts of the compound of Formula Ia, Ib or Ic. Examples of pharmaceutically acceptable salts include, but are not limited to, mineral or organic acid salts of basic residues such as amines; alkali or organic salts of acidic residues such as carboxylic acids; and the like.

"Prodrugs" are considered to be any covalently bonded carriers which release the active parent drug according to Formula Ia, Ib or Ic in vivo when such prodrug is administered to a mammalian subject. Prodrugs of the compounds of Formula Ia, Ib or Ic are prepared by modifying functional groups present in the compounds in such a way that the modifications are cleaved, either in routine manipulation or in vivo, to the parent compounds. Prodrugs include compounds of Formula Ia, Ib or Ic wherein hydroxyl, amino, sulfhydryl, or carboxyl groups are bonded to any group that, when administered to a mammalian subject, cleaves to form a free hydroxyl, amino, sulfhydryl, or carboxyl group respectively. Examples of prodrugs include, but are not limited to, acetate, formate and benzoate derivatives of alcohol and amine functional groups in the compounds of Formula Ia, Ib or Ic, and the like. Examples of representative carboxyl and amino prodrugs are included under the definition of R 2 , R 3 , and Y.

The pharmaceutically acceptable salts of the compounds of Formula Ia, Ib or Ic include the conventional non-toxic salts or the quaternary ammonium salts of the compounds of Formula Ia, Ib or Ic formed, for example, from non-toxic inorganic or organic acids. For example, such conventional non-toxic salts include those derived from inorganic acids such as hydrochloric, hydrobromic, sulfuric, sulfamic, phosphoric, nitric and the like; and the salts prepared from organic acids such as acetic, propionic, succinic, glycolic, stearic, lactic, malic, tartaric, citric, ascorbic, pamoic, maleic, hydroxymaleic, phenylacetic, glutamic, benzoic, salicylic, sulfanilic, 2-acetoxybenzoic, fumaric, toluenesulfonic, methanesulfonic, ethanesulfonic, ethanedisulfonic, oxalic, isethionic, and the like.

The pharmaceutically acceptable salts of the present invention can be synthesized from the compounds of Formula Ia, Ib or Ic which contain a basic or acidic moiety by conventional chemical methods. Generally, the salts are prepared by reacting the free base or acid with stoichiometric amounts or with an excess of the desired salt-forming inorganic or organic acid or base in a suitable solvent or various combinations of solvents.

The pharmaceutically acceptable salts of the acids of Formula Ia, Ib or Ic may be prepared by reacting the acid with an appropriate amount of a base, such as an alkali or alkaline earth metal hydroxide e.g. sodium, potassium, lithium, calcium, or magnesium, or an organic base such as an amine, e.g., dibenzylethylenediamine, trimethylamine, piperidine, pyrrolidine, benzylamine and the like, or a quaternary ammonium hydroxide such as tetramethylammonium hydroxide and the like.

›DETAILED DESCRIPTION OF THE INVENTION · 18 of 21

As discussed above, pharmaceutically acceptable salts of the compounds of the invention can be prepared by reacting the free acid or base forms of these compounds with a stoichiometric amount of the appropriate base or acid, respectively, in water or in an organic solvent, or in a mixture of the two; generally, nonaqueous media like ether, ethyl acetate, methanol, ethanol, isopropanol, or acetonitrile are preferred. Lists of suitable salts are found in Remington's Pharmaceutical Sciences, 17th ed., Mack Publishing Company, Easton, Pa., 1985, p. 1418, the disclosure of which is hereby incorporated by reference.

The disclosures of all of the references cited herein are hereby incorporated herein by reference in their entirety.

Synthesis

The compounds of the present invention can be prepared in a number of ways well known to one skilled in the art of organic synthesis. The compounds of the present invention can be synthesized using the methods described below, together with synthetic methods known in the art of synthetic organic chemistry, or variations thereon as appreciated by those skilled in the art. Preferred methods include, but are not limited to, those described below. All references cited herein are hereby incorporated in their entirety herein by reference.

Compounds of Formula Ia, Ib or Ic wherein X 1 , X 2 , X 3 and X 4 are all carbon and W is C(═O)NH can be prepared from appropriately substituted 4-, 5-, 6-, or 7-alkoxycarbonyl indazoles, IIIa, wherein R is an alkyl group such as methyl, ethyl or tert-butyl. ##STR42##

The requisite indazoles can be conveniently prepared from the commercially available nitrotoluic acids according to the example shown in Scheme 1. Conversion of the acid 1a to a suitable ester, such as the ethyl ester 1b, may be carried out by one of many methods well-known to one skilled in the art of organic synthesis, for example treatment with a suitable base, such as sodium bicarbonate, in a suitable solvent, such as N,N-dimethylformamide, followed by treatment with an alkyl halide, such as iodoethane. Reduction of the nitro group of 1b can be effected in a number of ways known to one skilled in the art of organic synthesis, including treatment with tin(II) chloride in ethanol. The resulting aniline derivative can be converted to the desired substituted indazole IIIa according to the method of Bartsch and Yang (J. Heterocycl. Chem. 1984, 21(4): 1063-1064). A variation of the conversion of the aniline 1c to the indazole IIIa proceeds through an N-acylated intermediate 1d followed by cyclization and deacetylation, according to the method reported by Ruchardt and Hassmann (Liebigs Ann. Chem. 1980, 908-927).

The order of the esterification and reduction steps may be reversed, such that the nitrotoluic acid is first converted to an aminotoluic acid, which is then esterified. In some cases other intermediates related to those shown in Scheme 1 are commercially available or may be prepared using methods described in the literature of organic chemistry; in these cases transformations similar to those shown in Scheme 1 may be used to prepare the desired compounds IIIa. For example, commercially available methyl 3-amino-4-methylbenzoate may be directly transformed into 6-methoxycarbonylindazole. ##STR43##

Compounds of Formula Ia or Ib wherein one or more of X 1 , X 2 , X 3 or X 4 are nitrogen may be prepared from the corresponding alkoxycarbonylindazoles IIIb in which the appropriate carbon atom or atoms have been replaced by nitrogen. These may in turn be prepared by substitution of the appropriately substituted heterocycle for the nitrotoluic acids, nitrotoluic acid esters, or aminotoluic acid esters in Scheme 1 above. The starting heterocycles could be obtained by following the procedures and methods in references outlined below, along with implementation of standard functional group transformations well known to one skilled in the art. ##STR44##

Functionalized pyrazines could be prepared according to procedures outlined in The Chemistry of Heterocyclic Compounds: The Pyrazines, Vol. 41 (Arnold Weissberger and Edward C. Taylor, Eds.),. John Wiley and Sons (New York: 1982). Preparation of appropriately functionalized pyridazines could be achieved using the methods described in The Chemistry of Heterocyclic Compounds: Condensed Pyridazines Including Cinnolines and Phthalazines, Vol. 27 (Arnold Weissberger and Edward C. Taylor, Eds.), John Wiley and Sons (New York: 1973) and The Chemistry of Heterocyclic Compounds: Pyridazines, Vol. 28 (Arnold Weissberger and Edward C. Taylor, Eds.), John Wiley and Sons (New York: 1973). For the synthesis of functionalized pyrimidines one could follow procedures in The Chemistry of Heterocyclic Compounds: The Pyrimidines, (Arnold Weissberger, Consulting Ed.) John Wiley and Sons (New York: 1962), The Chemistry of Heterocyclic Compounds: The Pyrimidines, Supplement I, (Arnold Weissberger and Edward C. Taylor, Consulting Eds.) John Wiley and Sons (New York: 1970), and The Chemistry of Heterocyclic Compounds: The Pyrimidines, Supplement II, Vol. 16 (Arnold Weissberger and Edward C. Taylor, Consulting Eds.) John Wiley and Sons (New York: 1985). Functionalized pyridines which can serve as starting materials in Scheme 1 could be made by the methods described in The Chemistry of Heterocyclic Compounds: Pyridine and Its Derivatives, Part Four, (Arnold Weissberger, Consulting Ed.) John Wiley and Sons (New York: 1964), The Chemistry of Heterocyclic Compounds: Pyridine and Its Derivatives, Supplement Part Two, (Arnold Weissberger and Edward C. Taylor, Consulting Eds.) John Wiley and Sons (New York: 1974), The Chemistry of Heterocyclic Compounds: pyridine and Its Derivatives, Supplement Part Three, Vol. 14 (Arnold Weissberger and Edward C. Taylor, Consulting Eds.) John Wiley and Sons (New York: 1974), The Chemistry of Heterocyclic Compounds: Pyridine and Its Derivatives, Supplement Part Four, Vol. 14 (Arnold Weissberger and Edward C. Taylor, Consulting Eds.) John Wiley and Sons (New York: 1975), and The Chemistry of Heterocyclic Compounds: Pyridine and Its Derivatives, Part Five, Vol. 14 (Arnold Weissberger and Edward C. Taylor, Consulting Eds.) John Wiley and Sons (New York: 1984). One example of the preparation of an appropriately substituted pyridine starting material is the preparation of 2-methyl-3-aminopyridine-5-carboxylic acid half-sulfate salt, as described by Argoudelis and Kummerow (J. Org. Chem. 1961, 26: 3420-3422).

›DETAILED DESCRIPTION OF THE INVENTION · 19 of 21

Compounds of Formula Ia wherein R 10 is not hydrogen may be prepared from appropriately substituted alkoxycarbonylindazoles. Some such substituted alkoxycarbonylindazoles may be prepared using the method outlined in Scheme 1. For example, methyl 4-amino-3-ethylbenzoate may be prepared as described by Witte and BoekeOheide (J. Org. Chem. 1972, 37 (18): 2849-2853) This compound may be converted to the diazonium fluoroborate and cyclized to 3-methyl-2-methoxycarbonylindazole using the method outlined in Scheme 1. This compound may be used as a starting material for preparation of the corresponding compounds of Formula Ia wherein R 10 is methyl.

Other substituted alkoxycarbonylindazoles may be prepared from unsubstituted alkoxycarbonylindazoles using the methods outlined in Scheme 2. For example, an ethoxycarbonylindazole may be brominated by treatment with bromine in a suitable solvent, such as acetic acid, to provide the corresponding 3-bromo-ethoxycarbonyl-indazole IIIc. This compound may be coupled with a suitable reagent, alternatively followed by additional synthetic manipulations, to provide the desired 3-substituted-ethoxycarbonylindazole. For example, coupling with phenylboronic acid in the presence of tetrakis-(triphenylphosphine)palladium and triethylamine in N,N-dimethylformamide, using the method of Miyaura, Suginome and Suzuki (Tetrahedron 1983, 2: 3271) provides the corresponding 3-phenyl-ethoxycarbonylindazole IIId. Similar methods, starting from compounds of Formula IIIb, may be used to prepare the corresponding compounds wherein one or more of the ring carbons (corresponding to those designated X 1 , X 2 , X 3 and X 4 in Formula Ia) are replaced by nitrogen. ##STR45##

As another example, also shown in Scheme 2, coupling of IIIc with phenylacetylene in the presence of bis-(triphenylphosphine)palladium(II) chloride, copper(I) chloride, and triethylamine in pyridine according to the method of Melissaris and Litt (J. Org. Chem. 1992, 57: 6998-6999) provides the corresponding 3-(2-phenylethynyl)-ethoxycarbonylindazole IIIe, which may be reduced using hydrogen in the presence of palladium on charcoal to provide the corresponding 3-(2-phenyl-ethyl)ethoxycarbonylindazole IIIf. Similar methods, starting from compounds of Formula IIIb, may be used to prepare the corresponding compounds wherein one or more of the ring carbons (corresponding to those designated X 1 , X 2 , X 3 and X 4 in Formula Ia) are replaced by nitrogen.

Compounds IIIc, IIId, IIIe and IIIf may be used in the preparation of compounds of Formula Ia in which R 10 is phenyl, 2-phenylethynyl, or 2-phenylethyl, respectively. Alternatively, further manipulations of the substituent may be accomplished at a later stage in the synthesis of the compound of Formula Ia. For example, the 2-phenylethynyl indazoles IIIe may be used in a synthetic sequence during the course of which the acetylene will be reduced, providing ultimately compounds of Formula Ia in which R 10 is 2-phenylethyl.

Other appropriately substituted alkoxycarbonylindazoles, for use in the preparation of compounds of Formula Ia wherein R 10 is not hydrogen, may be prepared using other methods known in the art of organic synthesis, such as those outlined in The Chemistry of Heterocyclic Compounds: Pyrazoles, Pyrazolines, Pyrazolidines, Indazoles and Condensed Rings, Vol. 22 (Arnold Weissberger, Ed.), John Wiley and Sons (New York: 1967), Chapter 10.

Hereinafter, unless otherwise specified, phrases such as "indazoles III" and "indazoles of Formula III" are meant to include simple indazoles IIIa, mono- or diazaindazoles IIIb, and substituted indazoles such as but not restricted to IIIc, IIId, IIIe and IIIf. Substituted mono- and diazaindazoles such as but not restricted to mono- and diaza analogs of IIIc, IIId, IIIe and IIIf are also included.

Compounds of Formula Ia may be prepared from indazoles III as outlined in Scheme 3. Alkylation of the indazoles of Formula III with a suitably functionalized alkyl halide can be effected in a variety of ways known to one skilled in the art. For example, using a method similar to that described by Granger et al. (Chim. Ther. 1970, 5: 24), an indazole of Formula III is treated with a suitable base, such as potassium bis(trimethylsilyl) amide, followed by addition of the alkyl halide, for example, 3-bromopropylphthalimide. Alternately, the alkylation can be carried out utilizing Mitsunobu conditions (Mitsunobu, Synthesis, 1981, 1-28) by addition of the corresponding alcohol, 3-hydroxypropylphthalimide, to a mixture of diethyl azodicarboxylate and triphenylphosphine in a suitable solvent, usually dry tetrahydrofuran, followed by addition of the indazole III. Separation, if necessary, of the mixture of 1- and 2-substituted isomers by chromatography provides the desired 1-alkylated product 3a. Removal of the phthalimide may be achieved by treatment with anhydrous hydrazine to give the primary amine 3b. ##STR46##

As further shown in Scheme 3,2-imidazolinyl-aminoalkylindazoles may be prepared by treatment of the amine 3b with a suitable reagent such as 2-methylthio-4,5-dihydroimidazolium iodide. Hydrolysis of the ester, using conventional methods known to one skilled in the art of organic synthesis, may be followed by coupling of the resulting acid to an appropriately substituted α- or β-amino ester such as a compound of Formula IV, to provide an intermediate which, after deprotection, affords compounds of Formula Ia wherein R 1 is 2-imidazolinylaminoalkyl. The coupling may be carried out using any of the many methods for the formation of amide bonds known to one skilled in the art of organic synthesis. Those methods include, but are not limited to, use of standard coupling procedures such as the azide method, mixed carbonic acid anhydride (isobutyl chloroformate) method, carbodiimide (dicyclohexylcarbodiimide, diisopropylcarbodiimide, or water-soluble carbodiimides (WSCDI)) method, active ester (p-nitrophenyl ester, N-hydroxysuccinic imido ester) method, or by the use of one of many other known coupling reagent such as BOP-Cl. Some of these methods (especially the carbodiimide method) can be enhanced by the addition of 1-hydroxybenzotriazole to the reaction mixture.

›DETAILED DESCRIPTION OF THE INVENTION · 20 of 21

An alternative method for preparing amines 3b wherein n=3 is outlined in Scheme 4. Alkylation of the indazole III may be achieved by treatment with an optionally substituted acrylonitrile in the presence of a catalytic amount of a base such as sodium ethoxide or sodium bis(trimethylsilyl)amide, in a suitable solvent such as ethanol, to provide the intermediate nitrile 4a. This may be converted to the amine 3b by reduction using any of a number of methods known to one skilled in the art of organic synthesis, such as by treatment with hydrogen in the presence of a catalyst such as palladium on charcoal. An acid such as aqueous hydrochloric acid may be added to the reaction mixture to minimize side reactions during the reduction. ##STR47##

Appropriately substituted racemic β-amino acids IV (used in Scheme 3) may be purchased commercially or, as is shown in Scheme 5, Method 1, prepared from the appropiate aldehyde, malonic acid and ammonium acetate according to the procedure of Johnson and Livak (J. Am. Chem. Soc., 1936, 58, 299). Racemic β-substituted-β-amino esters may be prepared through the reaction of dialkylcuprates or alkyllithiums with 4-benzoyloxy-2-azetidinone followed by treatment with anhydrous ethanol (Scheme 5, Method 2) or by reductive amination of β-keto esters as is described in WO93/16038 (also see Rico et al., J. Org. Chem., 1993, 58, 7948-51). Enantiomerically pure β-substituted-β-amino acids can be obtained through the optical resolution of the racemic mixture or can be prepared using numerous methods, including: Arndt-Eistert homologation of the corresponding β-amino acids as shown in Scheme 5, Method 3 (see Meier and Zeller, Angew. Chem. Int. Ed. Engl., 1975 14, 32; Rodriguez et al., Tetrahedron Lett., 1990, (31), 5153; Greenlee, J. Med. Chem. 1985, 28, 434 and references cited within); and through an enantioselective hydrogenation of a dehydroamino acid as is shown in Scheme 5, Method 4 (see Asymmetric Synthesis, Vol. 5, (Morrison, ed.) Academic Press, New York: 1985). A comprehensive treatise on the preparation of β-amino acid derivatives may be found in patent application WO 93/07867, the disclosure of which is hereby incorporated by reference. ##STR48##

The synthesis of N 2 -substituted diaminopropionic acid derivatives IV can be carried out via Hoffmann rearrangement of a wide variety of asparagine derivatives as described, for example, by Waki et al. (Synthesis 1981, 266-267) or by Moore et al. (J. Med. Chem. 1976, 19(6), 766-772). An example is shown in Scheme 6, Method 1. They may also be prepared by manipulations, which will be familiar to one skilled in the art of organic synthesis, of the commercially available 3-amino-2-benzyloxycarbonylaminopropionic acid. An example is shown in Scheme 6, Method 2. ##STR49##

Compounds of Formula Ia above wherein R 1 is 2-pyridinylaminoalkyl may be prepared by the method outlined in Scheme 7. Treatment of the intermediate aminoalkylindazole 3b from Scheme 3 (or the corresponding salt from Scheme 4) with 2-chloropyridine N-oxide hydrochloride, using a modification of the method described by Misra, et al. (Bioorg. and Med. Chem. Letters, 1994, 4, 2165-2170), and subsequent reduction of the resulting N-oxide derivative 7a provides a 2-pyridinylaminoalkyl intermediate 7b. This reduction may be performed using a number of methods known to one skilled in the art of organic synthesis, such as that using ammonium formate in the presence of 10% palladium on charcoal in refluxing ethanol, as described by Balicki (Synthesis, 1989, 645-646), or by reduction with hydrogen in the presence of a catalyst such as palladium on charcoal or Raney nickel, or by treatment with triphenylphosphine. The resulting 2-aminopyridine moiety of 7b may be optionally protected, for example by treatment with di-t-butyldicarbonate in dry tetrahydrofuran in the presence of a suitable base, such as triethylamine or N,N-dimethylaminopyridine, using the method of Iwanowicz (Synth. Commun., 1993, 23(10), 1443-1445), to provide intermediate 7c. Ester hydrolysis, coupling and deprotection as outlined in Scheme 3 can then provide the desired compounds of Formula Ia. ##STR50##

An alternative route to 1-(heteroarylaminoalkyl)indazoles of Formula Ia is outlined in Scheme 8. A suitable indazole III can be alkylated with an alkyl halide bearing a protected aldehyde, such as a 1,3-dioxolane, using conditions described above (see Scheme 3) to provide 8a. Deprotection to the aldehyde 8b, for example by treatment with aqueous acid, may be followed by reductive amination with a heteroarylamine such as 2-aminopyridine or a suitably protected 2-aminoimidazole, such as 1-triphenylmethyl-2-aminoimidazole, in the presence of a reducing agent such as sodium triacetoxyborohydride or sodium cyanoborohydride, to provide the 1-(heteroarylaminoalkyl)indazole 8c. The intermediates 8c can then be elaborated to the corresponding compounds of Formula Ia, for example as described in Scheme 3. ##STR51##

A route to 1-(heteroarylaminocarbonylethyl) 10 indazoles of Formula Ia is outlined in Scheme 9. A suitable indazole III can be alkylated by treatment with an acrylic acid ester such as tert-butyl acrylate, using a method such as that described in Scheme 4. Removal of the ester of 9a may be followed by conversion to a heteroaryl amide by treatment with a heteroaryl amine using any of a number of methods well known to one skilled in the art of organic synthesis. The resulting 1-(heteroarylaminocarbonylethyl)indazole 9b can then be elaborated to the corresponding compounds of Formula Ia, for example as described in Scheme 3. ##STR52##

Compounds of Formula Ib may be prepared according to the method outlined in Scheme 10. Thus, the appropriate indazole III may be alkylated by treatment with a suitable base, for example sodium hydride, followed by addition of a suitable alkylating agent such as an alkyl halide R 9 -Br or R 9 -I. Bromination of the intermediate 10a using, for example, bromine in acetic acid, provides the corresponding 3-bromo derivative 10b. (The order of these two synthetic steps may also be reversed. That is, the indazole III may be brominated, and resulting bromoindazole may be alkylated, to provide similar products 10b.) Coupling of 10b with, for example, 3,3-diethoxy-1-propyne, under conditions similar to those described by Sakamoto et al. (Synthesis 1992, 746-748) provides a functionallzed alkynyl derivative 10c. Reduction of the acetylenic bond of 10c using, for example, hydrogen in the presence of a catalyst such as palladium on charcoal, followed by hydrolysis of the acetal with aqueous acid provides an aldehyde intermediate 10d which, using methods analogous to those outlined in Scheme 8, may be elaborated to an intermediate 10e containing a heteroarylaminoalkyl substituent at the 3-position. This intermediate may then in turn be elaborated to the desired compounds of Formula Ib, for example using methods described in Scheme 3. ##STR53##

›DETAILED DESCRIPTION OF THE INVENTION · 21 of 21

Compounds of Formula Ib may alternatively be prepared from the intermediate 10b to the method described in Scheme 11. Thus,coupling of 10b under conditions similar to those described by Murakami et al. (Heterocycles, 1990, 31(8), 1505-11) can provide a 3-allyl derivative 11a. Hydroboration as described by Brown and Subba Rao (J. Am. Chem. Soc. 81, 6428-6433) can provide the alcohol 11b, which may be subjected to the Mitsunobu reaction (vide supra) with phthalimide followed by deprotection to provide an amine intermediate 11c which, analogously to the method shown in Schemes 10 and 3, can be elaborated to the desired compounds of Formula Ib. Alternatively, the intermediate 11b may be prepared by reduction of the aldehyde 10d shown in Scheme 10. Other methods can be used for the conversion of intermediates 10d and 11b to the primary amine 10c which are known to those skilled in the art of organic synthesis. ##STR54##

Compounds of Formula Ic may be prepared according to methods outlined in Scheme 12. Treatment of the appropriate indazole starting material 12a with zinc bromide and vinylmagnesium bromide followed by dichloro 1,1'-bis(diphenylphosphino)ferrocene! palladium (II), using a procedure similar to that described by Brown, et al. (U.S. Pat. No. 4,898,863), can provide the desired 3-vinyl derivative 12b. Treatment of this compound with ozone (F. J. Brown, et al. Ibid.), can provide an aldehyde 12c. Oxidation using silver(I) oxide, as described by Campaigne and LeSuer (Organic Syntheses, 1963, Coll. Vol. 4, 919), can provide the desired carboxylic acid 12d. Esterification and deprotection of the ether oxygen of 12e using boron tribromide, by a method analogous to that detailed by Manson and Musgrave (J. Chem. Soc. 1011 (1963)), can provide the hydroxy intermediate 12f. Mitsunobu coupling, (vide supra), followed by further transformations of 12g similar to those shown in Scheme 3, can provide compounds of Formula Ic. ##STR55##

Additional alcohols useful for the preparation of compounds of Formula Ia, Ib and Ic through the Mitsunobu reaction described in the above schemes may be prepared as described in Scheme 13. ##STR56##

Various compounds of Formula Ia, Ib or Ic may be prepared from a common derivative of the corresponding compounds of Formula Ia, Ib or Ic by functional group manipulations familiar to one skilled in the art of organic synthesis. As one example, preparation of compounds of Formula Ia having different sulfonamide substituents at R 16 may be achieved as outlined in Scheme 14. Thus, the compound of Formula Ia having a benzyloxycarbonylamino group at R 16 (14a) may be hydrogenolyzed using, for example, hydrogen in the presence of a catalyst such as palladium on charcoal to provide the primary amine derivative 14b. This may be reacted with a sulfonylating agent such as R 17 SO 2 Cl in the presence of an amine such as triethylamine to provide, after deprotection of the ester, the desired compound of Formula Ia. In place of the sulfonyl chloride, use of a carboxylic acid, acid chloride or acid anhydride can provide the corresponding amide derivative, use of a chloroformate can provide the corresponding carbamate derivative, use of a sulfamoyl chloride can provide the corresponding sulfamide derivative, and use of an isocyanate can provide the corresponding urea derivative. ##STR57##

As another example, compounds of Formula Ia with different variations in R 1 may be prepared from a common precursor as outlined in Scheme 15. Thus, the amine intermediate 3b may be reacted, for example, with benzyl chloroformate to provide the benzyl carbamate. Hydrolysis of the ester, for example with lithium hydroxide, can provide the acid intermediate 15a. Using methods described earlier, 15a may be reacted with, for example, a suitable beta-amino ester, followed by removal of the benzyl carbamate, for example by hydrogenolysis, to provide the amine intermediate 15b. Using, for example, steps analogous to those shown in Schemes 3 or 7, the amine may be converted to an aminoheterocyclic group. After deprotection of the ester, the desired compound of Formula Ia may be obtained. ##STR58##

The example outlined in Scheme 15 will also serve to demonstrate that the order in which the different substituents are elaborated to give the compounds of Formula Ia, Ib and Ic may be varied from that in the examples shown in Schemes 1 through 14. This example will also serve to demonstrate the use of protecting groups to temporarily protect a functional group in the course of a synthetic sequence when that functional group is not compatible with one or more of the synthetic transformations that are to be accomplished. Such use of protecting groups, while not always explicitly shown in Schemes 1 through 15, is well known to one skilled in the art of organic synthesis. Many examples of protecting groups may be found, for example, in Greene, "Protective Groups in Organic Syntheses", Wiley (New York), 1981.

The detailed processes for preparing the compounds of Formula Ia, Ib or Ic are illustrated by the following Examples. It is, however, understood that this invention is not limited to the specific details of these examples. Reactions were run under an atmosphere of nitrogen unless otherwise indicated. Solvent removal from reaction mixtures, extracts, and the like was performed under vacuum on a rotary evaporator. Flash chromatography refers to the medium-pressure column chromatography method described by Still et al. (J. Org. Chem. 1978, 43(14), 2923-2925). Melting points (mp) are uncorrected. Proton nuclear magnetic resonance spectra (NMR) were measured in chloroform-d (CDCl 3 ), dimethyl sulfoxide-d 6 (DMSO-d 6 ) or methanol-d 4 (MeOH-d 4 ) and the peaks are reported in parts per million downfield from tetramethylsilane (δ). The coupling patterns are reported as follows: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; b, broad. Mass spectra were measured using electrospray ionization (ESI),. ammonia chemical ionization (NH 3 --CI), fast-atom bombardment from a glycol matrix (FAB), or electron impact ionization (EI).

›Examples27

›EXAMPLE 1035b

3- 1- 3-(N-imidazol-2-ylamino)propyl!-indazol-5-ylcarbonyl-amino!-2(S)-(2 6-dimethyl-4-phenylbenzene-sulfonylamino)-propionic acid trifluoroacetate

A. tert-Butyl 3- 1- 3-(N-(1-triphenylmethylimidazol-2-yl)-amino)propyl!-indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionate

A mixture of the product prepared according to Example 1050e Part K (215 mg, 407 μmol, the product prepared according to Example 1178b Part E (140 mg, 407 μmol), 1-hydroxybenzotriazole hydrate (57 mg, 407 μmol) and N, N-dimethylformamide (5 μL) was treated with dicyclohexylcarbodiimide (870 mg, 407 μmol) and stirred at room temperature for 24 h. The mixture was poured into water (75 mL) and extracted with ethyl acetate (3×50 mL) The organic phase was drIed (MgSO 4 ) and concentrated under vacum. The residue was flash chromatographed (toluene:ethyl acetate, step gradient from 50:50 to 10:90) to provide the title product (262 mg, 75%) as a colorless glassy foam: 1 H NMR (CDCl 3 )δ8.17 (s, 1H), 7.97 (d, 1H), 7.73 (dd, 1H), 7.4-7.1 (15H), 6.99 (d, 1H), 6.94 (s, 2H), 6.85 (bt, 1H), 6.68 (d, 1H), 6.42 (d, 1H) 5.82 (bd, 1H), 4.07 (t, 2H), 3.93 (m, 1H), 3.83 (m, 1H), 3.62 (m, 1H), 3.04 (m, 1H), 2.97 (m, 2H), 2.65 (s, 6H), 2.26 (s, 3H) 1.82 (m, 2H), 1.32 (s, 9H); Mass spectrum (ESI) m/z 852.4 (100%, M+H + ).

Alternatively, a solution of the product prepared according to Example 1050e Part K (1.108 g, 2.1 mmol) in N,N-dimethylformamide (15 mL) was treated with the product prepared according to Example 1178b Part E (719 mg, 2.1 mmol), BOP reagent (975 mg, 2.2 mmol and diisopropylethyl-amine (543 mg, 4.2 mmol) and the mixture was stirred at room temperature overnight. The mixture was concentrated under vacuum and the residue was partitioned between ethyl acetate (100 mL) and water (25 mL). The aqueous phase was extracted with additional ethyl acetate (3×25 mL) and the combined organic phases were washed with hydrochloric acid (1.0N; 10 mL), water (2×10 mL), saturated aqueous sodium bicarbonate (10 mL) and brine (2×10 mL) then were dried (MgSO 4 ) and concentrated wider vacuum. This material was combined with the crude product from another run, starting from 10.8 g of the product prepared according to Example 1050e Part K (20.5 mmol), to provide the title product as a crude material; (23.0 g) which was used in the next step without purification.

B. tert-Butyl 3- 1- 3-(N-imidazol-2-ylamino)propyl!-indazol-5-ylcarbonylamino!-2(S)-(2,6-dimethyl-4-phenylbenzene-sulfonylamino)propionate

The product prepared according to Example 1035b Part A (3.3 g, 3.9 mmol) was combined with methanol (100 mL) and acetic acid (10 mL) and the mixture was heated at reflux overnight. The mixture was concentrated under vacuum, and the residue was flash chromatographed (chloroform: methanol:aqueous ammonia 100:10:1) to provide the product as a glassy foam. This was combined with the product from another run, starting from 19.0 g of the product prepared according to Example 1035b Part A (22.3 mmol), to provide the title product (4.5 g). Impure material from the column was re-chromatographed (chloroform: methanol:aqueous ammonia 100:5:0.5) to provide additional pure title product (6.5 g; total combined yield 81%): 1 H NMR (MeOH-d 4 ) δ 8.17 (d, 1H), 8.13 (d, 1H), 7.76 (dd, 1H), 7.57 (d, 1H), 6.85 (s, 2H), 6.51 (s, 2H), 4.53 (t, 2H), 4.06 (dd, 1H), 3.70 (dd, 1H), 3.50 (dd, 1H), 3.17 (t, 2H), 2.59 (S, 6H), 2.16 (m, 2H), 2.10 (s, 3H), 1.22 (s, 9H).

C. 3- 1- 3-(N-imidazol-2-ylamino)propyl!-indazol-5-yl-carbonylamino!-2(S)-(2,6-dimethyl-4-phenylbenzenesulfonyl-amino)propionic acid trifluoroacetate

A solution of the product prepared according to Example 1035b Part B (480 mg, 788 μmol) in dichloromethane (30 mL) was treated with trifluoroacetic acid (5 mL) and stirred for 1 h at room temperature. The solution was concentrated under vacuum, and the residue was dissolved in methanol (3 mL) and purified by preparative reverse-phase HPLC to provide, after lyophilization, the title product (432 mg, 82%) as an amorphous white solid: HPLC T R 12.33 min (95%); 1 H NMR (MeOH-d 4 ) δ 8.12 (s, 2H), 7.72 (dd, 1H), 7.54 (d, 1H), 6.76 (s, 2H), 6.73 (s, 2H), 4.53 (t, 2H), 4.16 (dd, 1H), 3.76 (dd, 1H), 3.49 (dd, 1H), 3.23 (t, 2H), 2.56 (s, 6H), 2.22 (m, 2H), 1.98 (s, 3H); High resolution mass spectrum (FAB) calculated (M+H + ) 554.2186, found 554.2196.

Alternatively, a solution of the product prepared according to Example 1035b Part A (249 mg, 292 μmol) in trifluoroacetic acid (2.5 mL) was heated at reflux for 60 min. The mixture was as cooled and concentrated, and the residue was purified by preparative reverse-phase HPLC to provide, after lyophilization, the title product (153 mg, 78%) as a white powder.

›EXAMPLE 1050e · 1 of 2

3- 1- 3-(N-imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid trifluoroacetate

A. Ethyl 3-methyl-4-nitrobenzoate

A mixture of 3-methyl-4-nitrobenzoic acid (1) (362.3 g, 2.0 mol), N,N-dimethylformamide (2000 mL), sodium bicarbonate (200 g, 2.38 mol) and iodoethane (623.9 g, 4.0 mol) was stirred at 70° C. for 18 h. The mixture was allowed to cool to room temperature and poured into water (2000 mL. The resulting solid was collected by filtration, washed with water and dried. The solid was washed further with hexane and dried to provide the title product (382.1 g, 91%) as an off-white solid: mp 51°-52.5° C.; 1 H NMR (CDCl 3 ) δ 8.04-7.98 (m, 3H), 4.42 (q, 2H), 2.63 (s, 3H), 1.42 (t, 3H); Mass spectrum (NH 3 --CI) m/z 210 (100%, M+H + ).

B. Ethyl 3-methyl-4-aminobenzoate

A mixture of the product prepared accordIng to Example 1050e Part A (183.96 g, 880 mol), tin (II) chloride hydrate (1025 g, 4.54 mol) and ethanol (3500 mL) was heated at reflux for 2 h. The mixture was cooled and diluted with water (3500 mL) and the pH was adjusted to 8.5. The mixture was diluted further with additional water, and extracted with ethyl acetate. The organic extracts were dried (MgSO 4 ), filtered and concentrated to provide the title product (136.62 g, 87%) as an off-white solid: mp 76°-78° C.; 1 H NMR (CDCl 3 ) δ 7.78 (s, 1H), 7.76 (d, 1H), 6.63 (d, 1H), 4,31 (q, 2H), 3.99 (bs, 2H), 2.19 (s, 3H), 1.38 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 180.1025, found 180.1023.

C. 5-Ethoxycarbonylindazole

A mixture of the product prepared according to Example 1050e Part B (250.55 g, 1.4 mol, potassium acetate (143.3 g, 1.46 mol), acetic anhydride 285.9 g, 2.8 mol) and chloroform (ethanol free; 2700 mL) was stirred at room temperature. The temperature rose to 40° C., then started to decline, at which time no starting material was detected by TLC. A mixture of 18-crown-6(75 g, 280 mmol) and n-amyl nitrite (364.5 g, 3.1 mol) was added and the mixture was heated at reflux overnight. The cooled mixture was washed with saturated aqueous sodium bicarbonate, then with water, and was dried (MgSO 4 ), filtered and concentrated under vacuum. The residue was combined with that from another batch (711.3 g) and distilled through a 10 cm vigreax column under vacuum to provide 1-Acetyl-5-ethoxcarbonyl-indazole (576 g, 82%), bp 115°-165° C. (1.0 Torr). This intermediate was combined with hydrochloric acid (6N; 2000 mL) and ethanol (2000 mL), and the mixture was stirred overnight at room temperature. The mixture was concentrated under vacuum and the solid was combined with water. The PH of the mixture was adjusted to 8 with aqueous ammonia, and the mixture was extracted with dichloromethane. The organic phase was concentrated to provide a solid (460 g). This was recrystallized from acetonitrile (1000 mL), and the crystals were washed with ethanol, then hexane, and dried to provide 5 (281 g, 60%) as a tan solid: mp 122°-124° C.; 1 H NMR (CDCl 3 ) δ 10.23 (bs, 1H), 8.57 (s, 1H), 8.20 (s, 1H), 8.10 (d, 1H), 7.53 (d, 1H), 4.42 (q, 2H), 1.42 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ); 191.0821, found 191.0838.

D. 1-(2-(1,3dioxolan-2-yl)ethyl)-5-ethoxycarbonylindazole

A solution of the product prepared according to Example 1050e Part C (74.5 g, 397 mol: in anhydrous tetrahydrofuran (1000 mL) was treated sequentially with sodium bis(trimethylsilyl)amide (1.0M in tetrahydrofuran; 430 mL, 430 mmol), 18-crown-6 (1.5 g) and 2(2bromoethyl)-1,3-dioxolane (90 g, 496 mmol). The solution was heated at reflux for 20 h, then was cooled to room temperature. The solvent was removed under vacuum, and the residue partitioned between toluene (2000 mL) and water (1000 mL). The aqueous phase was further extracted with toluene (3×200 mL), and the combined organic phases were washed with water (3×200 mL) and brine (2×200 mL). The organic phase was dried (MgSO 4 ) and concentrated under vacuum. The resulting oil was chromatographed with toluene, then with 185:15 toluene-ethyl acetate, to provide the title product (71.0 g, 55%): 1 H NMR (CDCl 3 ) δ 8.49 (s, 1H), 8.10 (s, 1H), 8.06 (d, 1H), 7.46 (d, 1H), 4.84 (t, 1H), 4.55 (t, 2H), 4.41 (q, 2H), 3.90 (m, 4H), 2.31 (m, 2H), 1.42 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 291.1345, found 291.1328.

E. 1-(3-oxopropyl) -5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1050e Part D (73.0 g, 256 mmol), acetic acid (365 g) and water (1020 mL) was heated at 70° C. for 20 h. The mixture was cooled to room temperature, extracted with dichloromethane (5×550 mL), and the combined organic layers were washed cautiously with saturated aqueous sodium bicarbonate (until no more gases were evolved), then with water (2×250 mL) and brine (2×250 mL). The organic layer was dried (MgSO 4 ), filtered and concentrated under vacuum to provide the title product (60.9 g, 98%) as a light yellow solid: 1 H NMR (CDCl 3 ) δ 9.87 (s, 1H), 8.50 (s, 1H), 8.10 (s+d, 2H), 7.51 (d, 1H), 4.70 (t, 2H), 4.41 (q, 2H), 3.19 (t, 2H), 1.42 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 247.1083, found 247.1068.

F. 2-Aminoimidazole

2Aminoimidazole sulfate (50 g, 378 mmol) was dissolved in methanol (1500 mL) and cooled to -78° C. Sodium methoxide (20.44 g, 378 mmol) was added portionwise over 60 min. The mixture stirred at -78° C. for 30 min, then at room temperature for 2.5 h. The solution was filtered through Celite® and concentrated under vacuum to provide 2-aminoimidazole as a semi-solid (32.5 g) which was used directly without further purification: 1 H NMR (DMSO-d 6 ) δ 6.32 (s, 2H), 5.0 (bs, 2H).

G. 2-Phthalimidoimidazole

A mixture of phthalic anhydride (57.3 g, 387.mmol) and the product prepared according to Example 1050e Part F (32.5 g, 387 mmol) was heated with mechanical stirring to 190°-200° C. for 20 min, then was placed under vacuum for 10 min. The mixture was cooled to room temperature and dried under vacuum for 24 h. This material (80 g, 99%) was used without further purification. It could be purified by flash chromatography (chloroform:methanol gradient from 95:5 to 80:20): 1 H NMR (DMSO-d 6 ) δ 12.35 (bs, 1H), 7.94-8.06 (m, 4H), 7.16 (bs, 2H); Mass spectrum (ESI) m/z 214.2 (100%, M+H + ).

›EXAMPLE 1050e · 2 of 2

H. 1Triphenylmethyl-2-phthalimidoimidazole

A solution of the product prepared according to Example 1050e Part G (80 g, 375 mmol) in dichloromethane (200 mL) was treated with triphenylmethyl chloride (314 g, 1.126 mol) and triethylamine (151.8 g, 1.5 mol). The mixture was heated at reflux for 5.5 h, then cooled to room temperature and concentrated under vacuum. The residue was extracted several times with hexane/ethyl acetate (70:30). The residual solid was dissolved in dichloromethane and washed several times with water, dried (MgSO 4 ) and concentrated. The residual solid was boiled in hexane, filtered, and the solid was washed several times with hot hexane until no trityl chloride was present by TLC. This provided the title product (119 g, 70%): 1 H NMR (CDCl 3 ) δ 7.64 (s, 4H), 7.28 (d, 6H), 7.17 (m, 7H), 7.06 (t, 3H),6.80 (d, 1H); Mass spectrum (NH 3 --CI) m/z 456 (100%, M+H + ).

I. 1-Triphenylmethyl-2aminoimidazole

A mixture of the product prepared according to Example 1050e Part H (114 g, 250 mmol), hydrazine (78. mL, 2.50 mol) and ethanol (3500 mL) was heated at reflux for 2 h. The mixture was cooled and the solvent was removed under vacuum. The solid residue was partitioned between water (500 mL) and chloroform (500 mL and the aqueous phase was extracted further with chloroform (3×200 mL). The combined organic layers were washed with water (2×200 mL), dried (MgSO 4 ) and concentrated to provide a sticky solid. This was heated with hexane and filtered to provide the title product (65 g, 80%) as a granular solid: 1 H NMR (DMSO-d 6 ) δ 7.33-7.44 (m, 9H), 7.13 (d, 6H), 6.51 (d, 1H), 6.26 (d, 1H); Mass spectrum (NH 3 --CI) 326 (100%, M+H + ).

J. 1- 3- N-(1-Triphenylmethylimidazol-2yl)amino!-propyl!-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1050e Part E (10.0 g, 40.6 mmol), the product prepared according to Example 1050e Part I (13.2 g, 40.6 mmol) and toluene (500 mL) was heated at reflux under a Dean-Stark trap. Toluene (3×100 mL) was removed while adding fresh dry toluene. The mixture fleas then heated further for 20 h, when NMR analysis of an aliquot showed the absence of aldehyde. The mixture was cooled to room temperature and sodium triacetoxyborohydride (34.42 g, 162.4 mmol) was added. The mixture was stirred at room temperature for 20 h, then was poured into water (500 mL). The layers were separated and the aqueous phase was extracted with ethyl acetate (3×100 mL). The combined organics were washed with saturated aqueous sodium bicarbonate (2×100 mL), water (2×100 mL) and brine (2×100 mL), then were dried (MgSO 4 ), fIltered and concentrated under vacuum to provide a crude product (25.0 g). This was combined with the crude product from another run (starting from 7.77 g of the product prepared according to Example 1050e Part E and 10.28 g of the product prepared according to Example 1050e Part I) and was purified by flash chromatography (toluene:ethyl acetate step gradient from 90:10 to 50:50) to provide the title product (21.0 g, 52%) as an oil which slowly solidified: 1 H NMR (CDCl 3 ) δ 8.45 (s, 1H), 7.97 (s, 1H) , 7.93 (d, 1H), 7.33 (m, 9H), 7.21 (m, 6H), 6.99 (d, 1H), 6.67 (d, 1H), 6.41 (d, 1H), 4.41 (q, 2H), 4.06 (t, 2H), 2.98 (m, 3H), 1.81 (m, 2H), 1.42 (t, 3H); High resolution mass spectrum (FAB) calculated (M+H + ) 556.2713, found 556.2725.

K. 1- 3- N-(1Triphenylmethylimidazol-2yl)amino!propylyl!-5-carboxyindazole

A mixture of the product prepared according to Example 1050e Part J (21.0 g, 37.8 mmol), ethanol (600 mL) and aqueous sodium hydroxide (1.0M; 209 mL, 209 mmol) was heated at reflux for 4 h. The mixture was cooled to room temperature and concentrated under vacuum to remove the ethanol. The pH of the residue was adjusted to 4, and the mixture was extracted with dichloromethane and the combined organic phases were dried (Na 2 SO 4 ). The mixture was filtered and the solids were washed with N,N-dimethylformamide to recover precipitated product. The combined filtrates were concentrated under vacuum and the residue was washed with ethanol and dried to provide the title product (16.9 g, 85%, as a white solid: 1 H NMR (DMSO-d 6 ) δ 8.39 (s, 1H), 8.13 (s, 1H), 7.87 (d, 1H), 7.36 (m, 10H), 7.12 (d, 6H), 6.51 (d, 1H), 6.28 (d, 1H), 4.05 (t, 2H), 2.84 (m, 2H), 1.63 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 528.2400, found 528.2418.

L. Methyl 3- 1- 3(N-(1-triphenylmethylimidazol-2-yl)amino)propyl!indazol-5-ylcarbonylamino!-2(S)-(2,6-dimethyl-4-phenylbenzenesulfonylamino)propionate

A mixture of the product prepared according to Example 1050e Part K (293 mg, 566 μmol), methyl 3amino-2(S)-(2,6-dimethyl-4-phenylbenzenesulfonyl)aminopropionate hydrochloride (prepared according to the method of Example 3093 Parts J and K described below; 290 mg, 727 μmol), N,N-dimethylformamide (7 mL), dicyclohexylcarbodiimide (115 mg, 557 μmol), 1-hydroxybenzotriazole hydrate (76 mg, 562 μmol) and triethylamine (230 μL, 1.65 mmol) was stirred at room temperature for 42 h. The mixture was concentrated under vacuum and the residue was purified by flash chromatography (ethyl acetate) to provide the title product (507 mg) contaminated with dicyclohexylurea, which was used in the subsequent reaction without further purification: 1 H NMR (CDCl 3 ) δ 8.13 (s, 1H), 8.02 (s, 1H), 7.70 (d, 1H), 7.60-7.15 (22H), 6.98 (d, 1H), 6.87 (t, 1H), 6.67 (d, 1H), 6.41 (d, 1H), 6.08 (bs, 1H), 4.05 (t, 2H), 3.95 (m, 1H), 3.75 (m, 1H), 3.65 (s, 3H), 3.47 (m, 1H), 2.95 (m, 2H), 2.75 (s, 6H), 1.79 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 872.3594, found 872.3593.

M. 3- 1- 3-(N-imidazol-2-ylamino)propyl!-indazol-5-ylcarbonylamino!-2(S)-(2,6-dimethyl-4-phenylbenzene-sulfonylamino) propionic acid trifluoroacetate

A mixture of the product prepared according to Example 1050e Part L (469 mg, 540 μmol), ethanol (13 mL) and aqueous sodium hydroxide (1.0M; 2.7 mL, 2.7 mmol) was heated at reflux for 90 min. The mixture was cooled to room temperature and concentrated, and the residue was taken up in trifluoroacetic acid (6 mL) and heated at reflux for 90 min. The mixture was cooled to room temperature and concentrated. The residue was purified by preparative reverse phase high pressure liquid chromatography (acetonitrile:water containing 0.05% trifluoroacetic acid; gradient from 10:90 to 90:10) to provide the title product (218 mg, 55%) as a white solid: 1 H NMR (MeOH-d 4 ) δ 8.06 (s, 1H), 7.95 (s, 1H), 7.63 (d, 1H), 7.34 (d, 1H), 7.28 (m, 5H), 7.09 (s, 2H), 6.75 (s, 2H), 4.34 (t, 2H), 4.27 (dd, 2H), 3.77 (dd, 1H), 3.47 (dd, 1H), 3.17 (t, 2H), 2.66 (s, 6H), 2.12 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 616.2342, found 616.2324.

›EXAMPLE 1081 · 1 of 2

3- 1- 3-(N-pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(benzyloxycarbonylamino)propionic acid trifluoroacetate

A. 1- 3-(N-phthalimido)-propyl!-5-ethoxycarbonylindazole

A mixture of tetrahydrofuran (50 mL) and 18-crown-6 (100 mg) was stirred at room temperature. Potassium bis(trimethylsilyl)amide (0.5M in toluene; 46.6 mL, 23.3 mmol) was added, followed by the product prepared according to Example 1050e Part C (4.43 g, 23.3 mmol) dissolved in dry tetrahydrofuran (50 mL). Then N-(3-bromopropyl)phthalimide (6.24 g, 23.3 mmol) dissolved in dry tetrahydrofuran (50 mL) was added. The mixture was heated at reflux for 16 h. The mixture was allowed to cool to room temperature and poured into water (200 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate 50:50) to provide the title product (4.25 g, 48%) as a yellow solid: mp 122°-124° C.; 1 H NMR (CDCl 3 ) δ 8.48 (s, 1H), 8.06 (s, 1H), 8.04 (d, 1H), 7.82 (m, 2H), 7.71 (m, 2H), 7.42 (d, 1H), 4.44 (t, 2H), 4.40 (q, 2H), 3.80 (t, 2H), 2.40 (m, 2H), 1.42 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 378.1454, found 378.1430. Also obtained (as a more polar fraction) was 2- 3-(N-phthalimido)propyl!-5-ethoxycarbonylindazole (2,75 g, 31%) as a yellow solid: mp 133°-135° C.; 1 H NMR (CDCl 3 ) δ 8.48 (s, 1H), 8.25 (s, 1H), 7.85 (d, 1H), 7.81 (m, 2H), 7.70 (m, 2H), 7.61 (d, 1H), 4.50 (t, 2H), 4.40 (q, 2H), 3.78 (t, 2H), 2.47 (m, 2H), 1.43 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 378.1454, found 378.1430.

B. 1-(3-aminopropyl)-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1081 Part A (2.10 g, 5.6 mmol), ethanol (35 mL), anhydrous tetrahydrofuran (35 mL) and anhydrous hydrazine (0.75 mL) was stirred at room temperature for 16 h. Dry tetrahydrofuran (100 mL) was added and the mixture was filtered. The filtrate was concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane:methanol 90:10 containing 1% triethylamine) to provide the title product (1.25 g, 91%) as an orange syrup: 1 H NMR (CDCl 3 ) δ 8.51 (s, 1H), 8.10 (s, 1H), 8.06 (d, 1H), 7.46 (d, 1H), 4.52 (t, 2H), 4.41 (q, 2H), 2.68 (t, 2H), 2.06 (m, 2H), 1.47 (bs, 2H), 1.43 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 248.1399, found 248.1392.

C. 1- 3- N-(1-oxido)pyridin-2-ylamino!propyl!-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1081 Part B (600 mg, 2.4 mmol), 2-chloropyridine-N-oxide hydrochloride (806 mg, 4.9 mmol), sodium bicarbonate (816 mg, 9.7 mmol) and n-butanol (7 mL) was stirred at 100° C. for 21 h. The mixture was allowed to cool to room temperature and was filtered. The filtrate was concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane:methanol 95:5) to provide the title product (675 mg, 81%) as a pale yellow solid, mp 87°-89° C.: 1 H NMR (CDCl 3 ) δ 8.52 (s, 1H), 8.15 (s, 1H), 8.13 (d, 1H), 8.03 (d, 1H), 7.39 (d, 1H), 7.10 (t, 1H), 6.93 (bt, 1H), 6.56 (t, 1H), 6.41 (d, 1H), 4.57 (t, 2H), 4.40 (q, 2H), 3.24 (q, 2H), 2.38 (m, 2H), 1.40 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 341.1614, found 341.1622.

D. 1- 3-(N-pyridin-2-ylamino)propyl!-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1081 Part C (62 mg, 182 μmol), 10% palladium on charcoal (8 mg) and ethanol (0.5 mL) was stirred at room temperature. Ammonium formate (63 mg, 1.0 mmol) was added and the mixture heated to reflux for 30 min. Additional 10% palladium on charcoal (8 mg) and 6ammonium formate (63 mg, 1.0 mmol) were added and the reaction was continued at reflux for 4 h. The mixture was allowed to cool to room temperature, filtered through Celite® and the solids were rinsed with ethanol. The solvent was evaporated from the filtrate under vacuum. The residue was purified by flash chromatography (dichloromethane:methanol 95:5) to provide the title product (31 mg, 52%) as a glass: 1 H NMR (CDCl 3 ) δ 8.52 (s, 1H), 8.12 (s, 1H), 8.06 (m, 2H), 7.38 (m, 2H), 6.55 (dd, 1H), 6.32 (d, 1H), 4.70 (bm, 1H), 4.53 (t, 2H), 4.40 (q, 2H), 3.30 (q, 2H), 2.24 (m, 2H), 1.42 (t, 3H); High resolution mass spectrum (NH3--CI) calculated (M+H + ); 325.1665, found 325.1659.

E. 1- 3-(N-tert-butyloxycarbonyl-N-pyridin-2-ylamino)-propyl!-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1081 Part D (80 mg, 246 mol), dry tetrahydrofuran (4 mL), triethylamine (0.3 mL) and N,N-dimethylaminopyridine (5 mg) was stirred at 0° C. Di-tert-butyldicarbonate (130 mg, 2.4 equiv.) was added and the mixture was stirred for 30 min. The ice bath was removed and the mixture was stirred at room temperature for 16 h. Additional di-tert-butyldicarbonate (130 mg, 2.4 equiv.) and N,N-dimethylaminopyridine (5 mg) were added and the mixture was stirred at room temperature for 72 h. The solvent was evaporated under vacuum and the residue was purified by flash chromatography (hexanes:ethyl acetate 65:35) to provide the title product (70 mg, 66%) as a clear oil: 1 H NMR (CDCl 3 ) δ 8.50 (s, 1H), 8.28 (m, 1H), 8.08 (s, 1H), 8.04 (d, 1H), 7.60 (m, 2H), 7.37 (d, 1H), 6.99 (m, 1H), 4.46 (t, 2H), 4.41 (q, 2H), 4.02 (t, 2H), 2.34 (m, 2H), 1.42 (t+s, 12H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ); 425.2189, found 425.2193.

F. 1- 3-(N-tert-butyloxycarbonyl-N-pyridin-2-ylamino)propyl!-5-carboxyindazole

A mixture of the product prepared according to Example 1081 Part E (7.9 g, 18.6 mmol), water (100 mL), ethanol (100 mL) and aqueous sodium hydroxide (1.0M; 40 ml, 40 mmol) was stirred at reflux for 16 h. The mixture was allowed to cool to room temperature and aqueous hydrochloric acid (1.0M; 43 mL, 43 mmol) was added. The solvent was decanted and the resulting gum was triturated several times with hexane to provide the title product (5.56 g, 75%) as a solid: mp 129°-131° C.; 1 H NMR (CDCl 3 ) δ 8.59 (s, 1H), 8.30 (m, 1H), 8.12 (s, 1H), 8.07 (d, 1H), 7.61 (m, 2H), 7.41 (d, 1H), 7.00 (m, 1H), 4.46 (t, 2H), 4.01 (t, 2H), 2.34 (m, 2H), 1.42 (s, 9H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ); 397.1876, found 397.1878.

›EXAMPLE 1081 · 2 of 2

G. tert-Butyl 3- 1- 3-(N-(tert-butyloxycarbonyl-N-pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(benzyloxycarbonylamino)propionate

A mixture of the product prepared according to the procedure of Example 1081 Part F (1.19 g, 3.0 mmol), tert-butyl 3-amino-2(S)-(benzyloxycarbonylamino)propionate (prepared according to Mokotoff and Logue, J. Med. Chem. 1981, 24, 554; 880 mg, 3.0 mmol), 1-hydroxybenzotriazole hydrate (410 mg, 3.0 mmol), and anhydrous tetrahydrofuran (20 mL) was stirred at room temperature. The mixture was treated with dicyclohexylcarbodiimide (660 mg, 3.2 mmol) and stirred for 24 h. The mixture was filtered and solvent was removed under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate 50:50) to provide the title product (1.81 g, 89%) as a glass: 1 H NMR (CDCl 3 ) δ 8.28 (d, 1H), 8.17 (s, 1H), 8.04 (s, 1H), 7.77 (d, 1H), 7.60 (d, 2H), 7.4-7.25 (m, 6H), 6.98 (m, 2H), 5.88 (bd, 1H), 5.13 (s, 2H), 4.47 (bm, 1H), 4.46 (t, 2H), 4.01 (t, 2H), 3.87 (m, 2H), 2.31 (m, 2H), 1.48 (s, 9H), 1.43 (s, 9H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 673.3350, found 673.3324.

H. 3- 1- 3-(N-pyridin-2ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(benzyloxycarbonylamino)propionic acid trifluoroacetate

A mixture of the product prepared according to Example 1081 Part G (32 mg, 47 μmol), dichloromethane (5 mL) and trifluoroacetic acid (300 μL) was stirred at room temperature for 16 h. The mixture was concentrated under vacuum and toluene was added. The solvent was evaporated and the residue was triturated with ether. The solvent was removed by decantation, and the residue was dried to constant weight under vacuum to provide the desired product (25 mg, 83%) as a hygroscopic white solid: 1 H NMR (DMSO-d 6 ) δ 8.57 (bm, 1H), 8.53 (bt, 1H), 8.26 (s, 1H), 8.21 (s, 1H), 7.82 (m, 3H), 7.69 (d, 1H), 7.59 (d, 1H), 7.28 (m, 5H), 6.93 (d, 1H), 6.78 (t, 1H), 4.99 (s, 2H), 4.52 (t, 2H), 4.23 (m, 1H), 3.60 (m, 2H), 3.24 (m, 2H), 2.15 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 517.2199, found 517.2213.

›EXAMPLE 1094

3- 1- 3-(N-pyridin-2ylamino)propyl!indazol-5-yl-carbonylamino!-2(S)-(isobutyloxycarbonylamino)propionic acid trifluoroacetate

A. tert-Butyl 3- 1- 3-(N-tert-butyloxycarbonyl-N-pyridin-2-ylamino)-propyl!indazol-5-ylcarbonylamino!-2(S)-aminopropionate

A mixture of the product prepared according to the procedure of Example 1081 Part G (1.60 g, 2.33 mmol), 10% palladium on charcoal (160 mg) and ethanol (30 mL) was placed in a pressure bottle and stirred at room temperature under an atmosphere of hydrogen (1 atmosphere pressure). After 5 h, the mixture was filtered through Celite®, the solids were rinsed with ethanol, and the filtrate was concentrated under vacuum to provide the title product (1.24 g, 97%) as a glass: 1 H NMR (CDCl 3 ) δ 8.28 (d, 1H), 8.20 (s, 1H), 7.82 (d, 1H), 7.60 (m, 2H), 7.38 (d, 1H), 6.98 (m, 1H), 6.93 (bt, 1H), 4.45 (t, 2H), 4.00 (t, 2H), 3.88 (m, 1H), 3.66 (m, 1H), 3.56 (m, 1H), 2.51 (m, 2H), 2.05 (bs, ca. 2H), 1.48 (s, 9H), 1.42 (s, 9H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 539.2982, found 539.2998.

B. tert-Butyl 3- 1- 3-(N-tert-butyloxycarbonyl-N-pyridin-2ylamino)-propyl!indazol-5-ylcarbonylamino-!2(S)-(isobutyloxycarbonylamino)propionate

A solution of the product prepared according to Example 1094 Part A (100 mg, 186 μmol) in N,N-dimethylformamide (5 mL) was treated with isobutyl chloroformate (27 μL, 205 μmol), 4-(N,N-dimethylamino)pyridine (10 mg) and pyridine (15 μL, 205 μmol). The solution was stirred at room temperature for 16 h, then was concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane:ethyl acetate 97:3) to provide the title product (106 mg, 89%) as a gum: 1 H NMR (DMSO-d 6 ) δ 8.51 (m, 1H), 8.28 (m, 2H), 8.22 (s, 1H), 7.96 (s, 1H), 7.9-7.50 (m, 3H), 7.53 (d, 1H), 7.11 (m, 1H), 4.46 (t, 2H), 4.21 (m, 1H), 3.84 (m, 2H), 3.75 (d, 2H), 3.69 (m, 1H), 3.56 (m, 1H), 2.13 (m, 2H), 1.83 (m, 1H), 1.33 (s, 9H), 1.30 (s, 9H), 0.88 (d, 6H); High resolution mass spectrum (FAB) calculated (M+H + ) calculated 639.3480, found 639.3506.

C. 3- 1- 3(N-pyridin-2ylamino)propyl!indazol-5-yl-carbonylamino!-2(S)-(isobutyloxycarbonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1081 Part H, the product prepared according to Example 1094 Part B (106 mg, 166 μmol) was converted to the title product (76 mg, 76%) as a solid: 1 H NMR (DMSO-d 6 ) δ 8.56 (m, 2H), 8.30 (s, 1H), 8.25 (s, 1H), 7.90-7.75 (m, 3H), 7.72 (d, 1H), 7.44 (d, 1H), 6.96 (d, 1H), 6.80 (t, 1H), 4.56 (t, 2H), 4.24 (m, 1H), 3.73 (d, 2H), 3.62 (m, 2H), 3.28 (m, 2H), 2.17 (m, 2H), 1.82 (m, 1H), 0.85 (d, 6H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) calculated 483.2348, found 483.2356.

›EXAMPLE 1099b

3- 1- 3(N-pyridin-2ylamino)propyl!indazol-5-yl-carbonylamino!-2-(S)-(E- phenylethenyl!carbonylamino)-propionic acid trifluoroacetate

A. tert-Butyl 3- 1- 3-(N-tert-butyloxycarbonyl-N-pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino-2(S)-(E- phenylethenyl!carbonylamino)propionate

A solution of the product prepared according to Example 1094 Part A (100 mg, 186 μmol) in tetrahydrofuran (3 mL) was treated with trans-cinnamic acid (28 mg, 186 μmol), 1-hydroxybenzotriazole hydrate (25 mg, 186 μmol) and dicyclohexylcarbodiimide (39 mg, 186 μmol). The mixture was stirred at room temperature for 18 h, then was concentrated under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate 70:30) to provide the title product (108 mg, 87%) as a gummy white solid: 1 H NMR (CDCl 3 ) δ 8.27 (d, 1H), 8.24 (s, 1H), 8.06 (s, 1H), 7.83 (d, 1H), 7.67 (d, J=17 Hz, 1H), 7.59 (m, 1H), 7.55-7.35 (m, 6H), 6.97 (m, 1H), 6.88 (d, 1H), 6.70 (d, J=17 Hz, 1H), 4.85 (m, 1H), 4.44 (t, 2H), 4.02 (m, 3H), 3.47 (m, 2H), 2.31 (m, 2H), 1.52 (s, 9H), 1.40 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 669.3401, found 669.3389.

B. 3- 1- 3-(N-pyridin-2-ylamino)propyl!indazol-5-yl-carbonylamino!-2(S)-(E- phenylethenyl!carbonylamino)propionate acid trifluoroacetate

Using the procedure of Example 1081 Part H, the product prepared according to Example 1099b Part A (100 mg, 150 μmol) was converted to the title product (90 mg, 96%) as a white solid: 1 H NMR (DMSO-d 6 ) δ 8.64 (t, 1H), 8.47 (d, 1H), 8.31 (s, 1H), 8.04 (s, 1H), 7.90-7.80 (m, 3H), 7.73 (d, 1H), 7.58 (d, 1H), 7.50-7.35 (m, 6H), 6.98 (d, 1H), 6.82 (t, 1H), 6.74 (d, J=17 Hz, 1H), 4.63 (m, 1H), 4.55 (t, 2H), 3.75-3.55 (m, 2H), 3.27 (m, 2H), 2.18 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 513.2250, found 513.2239.

›EXAMPLE 1108b

3-1- 3-(N-pyridin-2-ylamino)propyl!indazol-5-yl-carbonylamino!-2(S)-(cyclohexylcarbonylamino)propionic acid trifluoroacetate

A. 1- 3(pyridin-2-ylamino)propyl!-5-carboxyindazole

A mixture of the product prepared according to Example 1081 Part D (1.04 g, 3.19 mmol), ethanol (16 mL) and aqueous sodium hydroxide (1.0M; 16 ml, 16 mmol) was stirred at reflux for 20 h. The mixture was allowed to cool to room temperature and aqueous hydrochloric acid (1.0M; 16 mL, 16 mmol) was added. The resulting solid was collected by filtration, washed with water and dried to provide the title product: 1 H NMR (DMSO-d 6 ) δ 8.42 (s, 1H), 8.22 (s, 1H), 7.90 (m, 2H), 7.76 (d, 1H), 7.38 (m, 1H), 6.58 (t, 1H), 6.42 (m, 2H), 4.52 (t, 2H), 3.20 (q, 2H), 2.08 (m, 2H); Mass spectrum (ESI) m/z 297.3 (100%, M+H + ).

B. tert-Butyl 3- 1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(benzyloxycarbonylamino)propionate

Using the procedure of 1081 Part G, the product prepared according to the procedure of Example 1108b Part A (740 mg, 2.5 μmmol) was converted to the title product (700 mg, 56%): 1 H NMR (CDCl 3 ) δ 8.19 (s, 1H), 8.08 (s, 1H), 8.06 (m, 1H), 7.79 (d, 1H), 7.45-7.25 (m, 7H), 7.02 (bm, 1H), 6.56 (m, 1H), 6.32 (d, 1H), 5.90 (bm, 1H), 5.13 (s, 2H), 4.52 (t, 2H), 4.05 (bm, 1H), 3.87 (m, 2H), 3.47 (m, 1H), 3.28 (m, 2H), 2.26 (m, 2H), 1.48 (s, 9H); Mass spectrum (ESI) m/z 573.4 (22%, M+H + ).

C. tert-Butyl 3-1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-aminopropionate

Using the procedure of 1094 Part A, the product prepared according to the procedure of Example 1108b Part B (700 mg, 1.22 mmol) was converted to the title product (500 mg, 93%) as a gummy solid: 1 H NMR (CDCl 3 ) δ 8.24 (s, 1H), 8.09 (s, 1H), 8.01 (d, 1H), 7.84 (d, 1H), 7.47 (d, 1H), 7.40 (t, 1H), 7.10 (bm, 1H), 6.56 (t, 1H), 6.33 (d, 1H), 4.54 (t, 2H), 4.11 (m, 1H), 3.86 (m, 1H), 3.59 (m, 1H), 3.25 (m, 2H), 2.27 (m, 2H), 1.49 (s, 9H); Mass spectrum (ESI) m/z 439.3 (100%, M+H + ).

D. tert-Butyl 3- 1- 3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(cyclohexylcarbonylamino)propionate

Using the procedure of 1094 Part B, the product prepared according to the procedure of Example 1108b Part C (100 mg, 230 μmol) and cyclohexylcarbonyl chloride (31 μL, 230 μmol) were converted to the title product (60 mg, 50%): 1 H NMR (CDCl 3 ) δ 8.22 (s, 1H), 8.10 (s, 1H), 7.91 (d, 1H), 7.80 (d, 1H), 7.54 (d, 1H), 7.45 (m, 2H), 6.72 (d, 1H), 6.57 (t, 1H), 6.32 (d, 1H), 4.72 (m, 1H), 4.58 (t, 2H), 3.89 (m, 1H), 3.76 (m, 1H), 3.19 (t, 2H), 2.30 (m, 3H), 2.19 (m, 1H), 2.0-1.2 (m, 10H); Mass spectrum (ESI) m/z 549.5 (100%, M+H + ).

E. 3- 1- 3-(N-pyridin-2-ylamino)propyl!indazol-5-yl-carbonylamino!-2(S)-(cyclohexylcarbonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1081 Part H, the product prepared according to Example title product: 1 H NMR (DMSO-d 6 ) δ 8.54 (m, 1H), 8.28 (s, 1H), 8.25 (s, 1H), 8.02 (d, 1H), 7.9-7.7 (m, 4H), 6.90 (m, 1H), 6.77 (m, 1H), 4.55 (t, 2H), 4.44 (m, 1H), 3.61 (m, 2H), 3.26 (m, 2H), 2.16 (m, 3H), 2.0-1.0 (m, 10H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 493.2563, found 493.2559.

›EXAMPLE 1110a

3- 1- 3-(N-pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(phenylaminocarbonylamino)propionic acid trifluoroacetate

A. tert-Butyl 3- 1- 3-(N-tert-butyloxycarbonyl-N-pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(phenylaminocarbonylamino)propionate

A solution of the product prepared according to Example 1094 Part A (105 mg, 195 μmol) in dichloromethane (5 mL) was treated sequentially with diisopropylethylamine (69 μL, 385 μmol) and phenyl isocyanate (49 μl, 448 μmol). The solution was stirred at room temperature for 1 h, then was concentrated under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate, 50:50) to provide the title product (72 mg, 56%): 1 H NMR (CDCl 3 ) δ 8.25 (d, 1H), 8.18 (s, 1H), 7.95 (m, 1H), 7.86 (s, 1H), 7.75 (d, 1H), 7.70 (bm, 1H), 7.57 (m, 2H), 7.17 (m, 3H), 7.10 (m, 2H), 6.95 (m, 1H), 6.92 (m, 1H), 6.63 (m, 1H), 4.79 (m, 1H), 4.34 (t, 2H), 3.96 (m, 2H), 3.86 (m, 2H), 2.25 (m, 2H), 1.46 (s, 9H), 1.41 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 658.3353, found 658.3342.

B. 3- 1- 3-(N-pyridin-2-ylamino)propyl!indazol-5-yl-carbonylamino!-2(S)-(phenylaminocarbonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1081 Part H, the product prepared according to Example 1110a Part A (68 mg, 104 μmol) was converted to the title product (44 mg, 68%) as a white solid after preparative reverse phase high pressure liquid chromatography (acetonitrile:water containing 0.05% trifluoroacetic acid, gradient from 1:9 to 9:1): 1 H NMR (MeOH-d 4 ) δ 8.24 (s, 1H), 8.09 (s, 1H), 7.85-7.70 (m, 2H), 7.68 (d, 1H), 7.55 (d, 1H), 7.29 (m, 2H), 7.17 (t, 2H), 6.91 (m, 2H), 6.79 (t, 1H), 4.66 (m, 1H), 4.54 (t, 2H), 3.88 (dd, 1H), 3.77 (dd, 1H), 3.27 (m, 2H), 2.28 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 502.2203, found 502.2196.

›EXAMPLE 1129 · 1 of 2

3- 1- 3-(N-pyridin-2-ylamino)propyl!indazol-5-yl-carbonylamino!-2(S)-(1-naphthalene-sulfonylamino)-propionic acid trifluoroacetate

A. 1-(2-cyanoethyl)-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1050e Part C (3.80 g, 20 mmol), acrylonitrile (7.9 mL, 120 mmol), sodium bis-(trimethylsilyl)amide (1.0M in tetrahydrofuran; 1.0 mL, 1.0 mmol) and ethanol (40 mL) was heated to reflux. After 2 h, the solution was cooled to room temperature and treated with aqueous hydrochloric acid (1.0M; 1.5 mL, 1.5 mmol). After the mixture was partially concentrated under vacuum, a solid formed. Water (100 mL) was added and the mixture was stirred briefly. The resulting solid was collected by filtration, rinsed with water and dried to provide the title product (4.38 g, 90%) as a pale yellow fluffy solid: mp 106°-109° C.; 1 H NMR (CDCl 3 ) δ 8.54 (s, 1H), 8.16 (s, 1H), 8.13 (d, 1H), 7.48 (d, 1H), 4.70 (t, 2H), 4.42 (q, 2H), 3.03 (t, 2H), 1.43 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 244.1086, found 244.1070.

B. 1-(3-aminopropyl)-5-ethoxycarbonylindazole hydrochloride

A mixture of the product prepared according to Example 1129 Part A (60 g, 260 mmol), platinum oxide (6.0 g), ethanol (1600 mL) and chloroform (200 mL) was placed in a pressure bottle and agitated under an atmosphere of hydrogen (40 psig) for 19 h. The mixture was filtered through Celite® and the solids were washed with ethanol. The filtrate was concentrated under vacuum and the residue was dissolved in aqueous sodium bicarbonate and washed with ethyl acetate. The aqueous phase was acidified with hydrochloric acid and concentrated to a solid. This was dissolved in hot ethanol, filtered, and the filtrate cooled. The resulting crystals were collected by filtration to provide the title product. Repeating the reaction twice more starting with 57 g of the nitrile provided a total of 115 g (57%) of the title product as a white solid: mp 198°-200° C.; 1 H NMR (DMSO-d 6 ) δ 8.49 (s, 1H), 8.32 (s, 1H), 8.07 (bs, 3H), 7.98 (d, 1H), 7.85 (d, 1H), 4.58 (t, 2H), 4.34 (q, 2H), 2.80 (bm, 2H), 2.14 (m, 2H), 1.34 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 248.1399, found 248.1396.

C. 1- 3- N-(1-oxido)pyridin-2-ylamino!propyl!-5-ethoxycarbonylindazole

Using the procedure of Example 1081 Part C, the product prepared according to Example 1129 Part B (566 mg, 2.0 mmol) was converted to the title product (470 mg, 69%). This product is the same as the product of Example 1081 Part C.

D. 1- 3- N-(1-oxido)pyridin-2-ylamino!propyl!-5-carboxyindazole

A mixture of the product prepared according to Example 1129 Part C (470 mg, 1.3 mmol), aqueous sodium hydroxide (1.0M; 4.0 moL, 4.0 mmol), water (10 mL) and ethanol (10 mL) was heated to reflux. After 30 h, additional aqueous sodium hydroxide (1.0M; 2.0 mL) was added and heating was continued. After 48 h more, the mixture was cooled to room temperature and treated with aqueous hydrochloric acid (1.0M; 6.0 mL) to give a precipitate. The solid was collected by filtration, rinsed with water and dried to provide the title product (369 mg, 91%) as a white solid: 1 H NMR (DMSO-d 6 ) δ 12.70 (bs, 1H), 8.45 (s, 1H), 8.27 (s, 1H), 8.11 (d, 1H), 7.92 (d, 1H), 7.73 (d, 1H), 7.32 (bt, 1H), 7.16 (t, 1H), 6.70 (d, 1H), 6.59 (t, 1H), 4.53 (t, 2H), 3.24 (q, 2H), 2.14 (m, 2H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 313.1301, found 313.1299.

E. tert-Butyl 3- 1- 3-(N-(1-oxido)pyridin-2-ylamino)-propyl!indazol-5-ylcarbonylamino!-2-(S)-(benzyloxy-carbonylamino)propionate

A mixture of the product prepared according to Example 1129 Part D (312 mg, 1.0 mmol), tert-butyl 3-amino-2(S)-benzyloxycarbonylaminopropionate (prepared according to Mokitoff and Logue, J. Med. Chem. 1981, 24, 554; 294 mg, 1.0 mmol), 1-hydroxybenzotriazole hydrate (135 mg, 1.0 mmol), tetrahydrofuran (4 mL) and dry N,N-dimethylformamide (1 mL) was stirred on an ice bath. Dicyclohexylcarbodiimide (227 mg, 1.1 mmol) was added, and the mixture was stirred for 1 h. The ice bath was removed and stirring was continued for 3.5 h more. The mixture was filtered, and the solid was rinsed with tetrahydrofuran. The filtrate was concentrated under vacuum, and the residue was taken up in ethyl acetate. The solution was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane/methanol; 96:4, then 94:6) to provide the title product (304 mg, 52%) as an off-white glass: 1 H NMR (CDCl 3 ) δ 8.00 (s, 1H), 8.11 (d, 1H), 8.07 (s, 1H), 7.76 (d, 1H), 7.4-7.2 (m, 6H), 7.18 (bt, 1H), 7.12 (t, 1H), 6.95 (bt, 1H), 6.53 (t, 1H), 6.39 (d, 1H), 6.10 (d, 1H), 5.11 (s, 2H), 4.50 (t, 3H),3.88 (m, 2H), 3.21 (q, 2H), 2.31 (m, 2H), 1.48 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 589.2775, found 589.2804.

F. tert-Butyl 3- 1- 3-(N-pyridin-2ylamino)-propyl!-indazol-5-ylcarbonylamino!-2-(S)-aminopropionate

A mixture of the product prepared according to Example 1129 Part E (266 mg, 452 mol) and 10% palladium on charcoal (65 mg) in ethanol (20 mL) was placed in a pressure bottle and agitated under an atmosphere of hydrogen (55 psig) for 100 h. The mixture was filtered through Celite® and the solids were rinsed with ethanol. The filtrate was concentrated under vacuum, and the residue was purified by flash chromatography (dichloromethane:methanol, step gradient from 96:4, to 92.5:7.5) to provide the title product (100 mg, 50%) as a colorless glass: 1 H NMR (CDCl 3 ) δ 8.21 (s, 1H), 8.10 (s, 1H), 8.07 (d, 1H), 7.80 (d, 1H), 7.42 (d, 1H), 7.39 (t, 1H), 6.88 (bt, 1H), 6.56 (t, 1H), 6.33 (d, 1H), 4.90 (bt, 1H), 4.53 (t, 2H), 3.86 (m, 1H), 3.63 (m,1H), 3.52 (m, 1H), 3.28 (q, 2H), 2.26 (m, 2H), 1.90 (b, 2H), 1.48 (s, 9H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 439.2458, found 439.2457.

G. tert-Butyl 3- 1- 3-(N-pyridin-2-ylamino)-propyl!-indazol-5-ylcarbonylamino!-2-(S)-(1-naphthalenesulfonylamino)propionate

›EXAMPLE 1129 · 2 of 2

A solution of the product prepared according to Example 1129 Part F (77 mg, 176 μmol) in dry tetrahydrofuran (2 mL) was treated with 4-(N,N- dimethylamino)pyridine (24 mg, 193 μmol), 1-naphthalenesulfonyl chloride (44 mg, 193 μmol) and pyridine (16 μL, 193 μmol). The mixture was stirred at room temperature for 20 h, then was concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane-methanol, 96:4) and rotary thin-layer chromatography (dichloromethane-methanol, 96:4) to provide the title product (90 mg, 82%) as a colorless glass: 1 H NMR (CDCl 3 ) δ 8.67 (d, 1H), 8.26 (d, 1H), 8.1-8.0 (m, 4H), 7.88 (d, 1H), 7.70 (m, 2H), 7.56 (m, 2H), 7.20 (m, 2H), 6.60 (m, 2H), 6.34 (d, 1H), 6.10 (bs, 1H), 5.35 (bs, 1H), 4.53 (t, 2H), 3.95 (b, 1H), 3.80 (m, 1H), 3.63 (m, 1H), 3.28 (q, 2H), 2.28 (m, 2H), 1.12 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 629.2546, found 629.2526.

H. 3- 1- 3-(N-pyridin-2-ylamino)-propyl!indazol-5-ylcarbonylamino!-2-(S)-(1-naphthalenesulfonylamino)propionic acid trifluoroacetate

A solution of the product prepared according to Example 1129 Part G (77 mg, 122 μmol) in dichloromethane (2 mL) was treated with trifluoroacetic acid (1 mL) and stirred at room temperature for 3 h. The solution was concentrated under vacuum, toluene was added, and the solvent was again removed under vacuum. The residue was triturated in ether, and the resulting solid was collected by filtration to provide the title product (81 mg, 96%) as a white powder: 1 H NMR (DMSO-d 6 ) δ 8.60 (m, 3H), 8.39 (bt, 1H), 8.21 (s, 1H), 8.09 (d, 2H), 8.05 (s, 1H), 7.90 (t, 2H), 7.83 (t, 1H), 7.67 (m, 3H), 7.55 (m, 2H), 6.97 (d, 1H), 6.81 (t, 1H), 4.56 (t, 2H), 4.08 (q, 1H), 3.53 (m, 1H), 3.30 (m, 3H), 2.18 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 573.1947, found 573.1928.

›EXAMPLE 1129a

3- 1- 3-(N-pyridin-2ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(4-phenylbenzenesulfonylamino)propionic acid trifluoroacetate

A. tert-Butyl 3- 1- 3-(N-tert-butyloxycarbonyl-N-pyridin-2ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(4-phenylbenzenesulfonylamino)propionate

Using the procedure of Example 1129 Part G, the product prepared according to Example 1094 Part A (86 mg, 159 μmol) and 4-phenylbenzenesulfonyl chloride were converted to the title product (116 mg, 97%): 1 H NMR (CDCl 3 ) δ 8.28 (m, 1H), 8.23 (2, 1H), 8.06 (s, 1H), 7.92 (d, 2H), 7.81 (d, 1H), 7.68 (d, 2H), 7.60 (m, 2H), 7.53 (m, 2H), 7.45 (m, 3H), 7.37 (d, 1H), 6.99 (m, 1H), 6.88 (bt, 1H), 5.75 (d, 1H), 4.45 (t, 2H), 4.01 (m, 4H), 3.62 (m, 1H), 2.31 (m, 2H), 1.43 (s, 9H), 1.30 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 755.3227, found 755.3200.

B. 3- 1- 3-(N-pyridin-2ylamino)propyl!indazol-5-yl-carbonylamino!-2(S)-(4-phenylbenzenesulfonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1129 Part H, the product prepared according to Example 1129 a Part A (108 mg, 143 μmol) was converted to the title product: 1 H NMR (MeOH-d 4 ) δ 8.16 (s, 1H), 8.08 (s, 1H), 7.85 (d, 2H), 7.8-7.7 (m, 4H), 7.58 (d, 2H), 7.5-7.3 (m, 6H), 6.9-6.75 (m, 2H), 4.48 (t, 2H), 4.23 (m, 1H), 3.78 (dd, 1H), 3.50 (dd, 1H), 3.26 (m, 2H), 2.26 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 599.2077, found 599.2062.

›EXAMPLE 1155

3- 1- 3-(N-pyridin-2-ylamino)propyl!indazol-5-yl-carbonylamino!-2(S)-(benzylaminiosulfonylamino)propionic acid trifluoroacetate

A. tert-Butyl 3- 1- 3-(N-(tert-butyloxycarbonyl-N-pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(benzylaminosulfonylamino)propionate

A solution of the product prepared according to Example 1094 Part A (101 mg, 188 μmol) in anhydrous tetrahydrofuran (5 mL) was treated with N-benzylsulfamoyl chloride (prepared according to the procedures of Audrieth and Sveda, J. Org. Chem. 1944, 9, 89-101, and Kloeck and Leschinsky, J. Org. Chem. 1976, 41, 4028-4029; 51 mg, 248 μmol), then with 4-(N,N-dimethylamino)pyridine (37 mg, 193 μmol) and pyridine (19 μL, 252 μmol). The resulting mixture was stirred at room temperature for 24 h, then was concentrated under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate 45:55) to provide the title product (92 mg, 70%) as a white solid: 1 H NMR (CDCl 3 ) δ 8.27 (m, 1H), 8.18 (s, 1H), 8.04 (s, 1H), 7.78 (d, 1H), 7.60 (m, 2H), 7.36 (d, 1H), 7.29 (m, 5H), 6.99 (m, 1H), 6.79 (bt, 1H), 5.62 (d, 1H), 4.75 (t, 1H), 4.44 (t, 2H), 4.23 (t, 2H), 4.15 (m, 1H), 4.00 (m, 2H), 3.95 (m, 1H), 3.76 (m, 1H), 2.31 (m, 2H), 1.48 (s, 9H), 1.43 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 708.3179, found 708.3205

B. 3- 1- 3-(N-pyridin-2yl)aminoproply!indazol-5-yl!-carbonylamino-2(S)-benzylaminosulfonylaminopropionic acid trifluoroacetate

Using the procedure of Example 1129 Part H, the product prepared according to Example 1155 Part A (21 mg, 30 μmol) was converted to the title product (19 mg, 96%): 1 H NMR (DMSO-d 6 ) δ 8.56 (m, 2H), 8.33 (s, 1H), 8.24 (s, 1H), 7.90-7.70 (m, 4H), 7.49 (d, 1H), 7.43 (t, 1H), 7.23 (m, 5H), 6.96 (d, 1H), 6.80 (t, 1H), 4.56 (t, 2H), 4.20-3.60 (m, 5H), 3.59 (m, 2H), 2.18 (t, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 552.2029, found 552.2042.

›EXAMPLE 1178b · 1 of 2

3- 1- 3-(N-3 4,5,6-Tetrahydropyrimidin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

A. 1-(3-Benzyloxycarbonylaminopropyl)-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1129 Part B (5.0 g, 18 mmol) and triethylamine (7.5 mL, 19 mmol) in dichloromethane (100 mL) was cooled on an ice bath and treated with benzyl chloroformate (2.7 mL, 19 mmol). The mixture was stirred at room temperature for 16 h, then was concentrated under vacuum. The residue was dissolved in dichloromethane and washed with water several times, then was dried over anhydrous magnesium sulfate, filtered and concentrated to provide the title product (3.4 g, 49%) as a white solid. While this material was suitable for further use, it could be purified by flash chromatography (dichloromethane:methanol 95:5): 1 H NMR (CDCl 3 ) δ 8.50 (s, 1H), 8.06 (m, 2H), 7.38 (m, 6H), 5.20 (bm, 1H), 5.02 (s, 2H), 4.42 (m, 4H), 3.18 (m, 2H), 2.18 (m, 2H), 1.40 (m, 3H); Mass spectrum (ESI) m/z 382.5 (100%, M+H + ).

B. 1-(3-Benzyloxycarbonylaminopropyl)-5-carboxyindazole

A mixture of the product prepared according to Example 1178b Part A (3.08 g, 8.07 mmol), lithium hydroxide hydrate (678 mg, 16.2 mmol), ethanol (160 mL) and water (40 mL) was stirred at room temperature. Tetrahydrofuran was added until the mixture was homogeneous, then stirring was continued for 5 days. The solution was concentrated, and the residue was taken up in water. The mixture was washed with ethyl acetate, and the aqueous phase was acidified to pH 4-5 with aqueous hydrochloric acid (1.0M). This mixture was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated to provide the title product (1.6 g, 56%) as a sticky solid: 1 H NMR (DMSO-d 6 ) δ 8.44 (s, 1H), 8.26 (s, 1H), 7.93 (d, 1H), 7.72 (d, 1H), 7.35 (m, 5H), 5.00 (s, 2H), 4.46 (t, 2H), 3.01 (m, 2H), 1.98 (m, 2H).

C. N 2 -(2,4,6 trimethylbenzenesulfonyl)-L-asparagine

L- Asparagine (20.0 g, 0.15 mol) was suspended in a mixture of tetrahydrofuran (130 mL) and water (250 mL). Triethylamine (68 mL, 0.48 mol) was added, followed by mesitylenesulfonyl chloride (49.7 g, 0.23 mol) added over 20 min. The reaction mixture became slightly warmer and the solids dissolved to yield a yellow solution. The reaction mixture was stirred for 3 h at room temperature, then washed twice with ether, and twice with dichloromethane. The aqueous layer was acidified to pH 1.5 with concentrated aqueous HCl, during which time a thick precipitate formed. After being stirred for 30 min the solid was collected by filtration, washed with water and dried to yield the title product (34.1 g, 72%) as a white solid: m.p. 193.5°-195° C.; 1 H NMR (DMSO-d 6 ) δ12.58 (bs, 1H), 7.82 (d, 1H), 7.32 (bs, 1H), 6.99 (s, 2H), 6.88 (bs, 1H) 3.98 (m, 1H), 2.55 (s, 6H), 2.45 (dd, 1H), 2.28 (dd, 1H), 2.24 (s, 3H); Mass spectrum (ESI) m/z 315.2, (100%, M+H + ).

D. 3-Amino-2-(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid

Sodium hydroxide (32 g, 0.80 mol), was dissolved in water (200 mL) and cooled in an ice bath.

Bromine (6.2 mL, 0.12 mol) was added dropwise over 5 min and the mixture was allowed to stir for 15 min. The product prepared according to Example 1178b Part C (31.44 g, 0.10 mol) was added in several portions over a period of ca. 10 min, during which time the yellow color faded. After stirring for 15 min more, the reaction mixture was heated rapidly to an internal temperature of ca. 85° C. After 1 h, the reaction mixture was allowed to cool to room temperature, then cooled in an ice bath. The reaction mixture was cautiously acidified to pH 6 with concentrated aqueous HCl, during which time a solid formed and gas was evolved. The solid was collected by filtration, washed with cold water, and allowed to dry overnight to provide the title product (23.9 g, 83%) as a white solid: 1 H NMR (DMSO-d 6 ) δ 7.06 (s, 2H), 3.07 (dd, 1H), 3.35 (broad), 2.94 (dd, 1H), 2.80 (dd, 1H), 2.59 (s, 6H), 2.26 (s, 3H); Mass spectrum (ESI) m/z 287.2 (100%, M+H + ).

E. tert-Butyl 3-amino-2-(S)-(2,4,6-trimethylbenzenesulfonylamino)propionate

The product prepared according to Example 1178b Part D (11.45 g, 0.04 mol) was placed in a pressure bottle and dissolved in dioxane (170 mL). Concentrated sulfuric acid (11 mL) was added and the reaction mixture was cooled in a dry ice-acetone bath. Liquid isobutylene (ca. 185 mL) was added, and the bottle was sealed and agitated for 114 h. The bottle was de-pressurized, then purged with nitrogen for a brief time. The reaction mixture was poured into a rapidly stirred mixture of water (225 mL) containing sodium hydroxide (17 g) and ether (600 mL) which had been pre-cooled in an ice bath. The layers were separated, and the aqueous layer was extracted with additional ether. These organic extracts were discarded. The pH of the aqueous layer was carefully adjusted with concentrated aqueous HCl to pH 11.0 and extracted four times with ether. The organic layers from the pH 11 extraction were combined, dried with anhydrous sodium sulfate, filtered and concentrated to yield the title product (8.64 g, 63%) as a viscous oil which gradually solidified: 1 H NMR (CDCl 3 ) δ 6.95 (s, 2H), 3.69 (m, 1H), 2.93 (m, 2H), 2.67 (s, 6H), 2.28 (s, 3H), 1.28 (s, 9H); Mass spectrum (ESI) m/z 343.3 (100%, M+H + ).

F. tert-Butyl 3- 1-(3-benzyloxycarbonylaminopropyl)indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionate

Using the procedure of Example 1129 Part E, the product prepared according to Example 1178b Part B (100 mg, 283 μmol) and the product prepared according to Example 1178b Part E (107 mg, 283 μmol) were converted to the title product (130 mg, 68%) as a yellowish solid: 1 H NMR (CDCl 3 ) δ 8.24 (s, 1H), 8.09 (s, 1H), 7.85 (d, 1H), 7.42 (d, 1H), 7.36 (m, 5H), 6.93 (s, 2H), 6.83 (m, 1H), 5.78 (d, 1H), 5.09 (s, 2H), 4.47 (t, 2H), 4.02 (m, 1H), 3.84 (m, 1H), 3.7-3.4 (m, 2H), 3.18 (m, 2H), 2.66 (s, 6H), 2.26 (s, 3H), 2.15 (m, 2H), 1.21 (s, 9H); Mass spectrum (ESI) m/z 678.4 (41%, M+H + ).

›EXAMPLE 1178b · 2 of 2

G. tert-Butyl 3- 1-(3-aminopropyl)-indazol-5-yl-carbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionate

A mixture of the product prepared according to Example 1178b Part F (50 mg, 74 μmol), palladium hydroxide on charcoal (Pearlman's catalyst; 15 mg), 1,4-cyclohexa-diene (1 mL) and methanol (2 mL) was heated at reflux. After 4 h, the mixture was cooled and filtered through Celite®, and the solids were rinsed with methanol. The filtrate was concentrated under vacuum to provide the title product (34 mg, 85%) as a solid which was used in subsequent reactions without further purification: 1 H NMR (CDCl 3 ) δ 8.03 (s, 1H), 7.80-7.65 (m, 3H), 7.31 (d, 1H), 6.84 (s,H), 4.40 (m, 2H), 4.02 (m, 1H), 3.78 (m, 2H), 3.06 (m, 2H), 2.63 (m, 1H), 2.59 (s, 6H), 2.27 (m, 2H), 2.19 (s, 3H), 1.23 (s, 9H); Mass spectrum (ESI) m/z 544.5 (100%, M+H + ).

H. tert-Butyl 3- 1- 3-(N-3,4,5,6-tetrahydropyrimidin-2-ylamino)propyl!-indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionate hydriodide

A mixture of the product prepared according to Example 1178b Part G (100 mg, 184 μmol) and 2methylthio-3,4,5,6-tetrahydropyrimidine hydriodide (57 mg, 221 μmol) in pyridine (5 mL) was heated at 120° C. After 16 h, the mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane:methanol, step gradient from 95:5 to 90:10) to provide the title product (37 mg, 27%): 1 H NMR (CDCl 3 ) δ 8.30 (s, 1H), 8.10 (bm, 1H), 8.08 (s, 1H), 7.92 (d, 1H), 7.85 (t, 1H), 7.51 (d, 1H), 7.10 (bt, 1H), 6.95 (s, 2H), 4.47 (m, 2H), 3.95 (m, 1H), 3.85 (m, 1H), 3.61 (m, 1H), 3.44 (m, 4H), 3.27 (m, 2H), 2.64 (s, 6H), 2.28 (s, 3H), 2.15 (m, 2H), 2.00 (m, 2H), 1.30 (s, 9H); Mass spectrum (ESI) m/z 626.5 (100%, M+H + ).

I. 3- 1- 3-(N-3,4,5,6-Tetrahydropyrimidin-2ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1129 Part H, the product prepared according to Example 1178b Part H was converted to the title product: 1 H NMR (DMSO-d 6 ) δ 8.46 (bt, 1H), 8.24 (s, 1H), 8.19 (s, 1H), 8.07 (d, 1H), 7.79 (d, 1H), 7.32 (bt, 1H), 6.84 (s, 2H), 4.47 (t, 2H), 4.02 (m, 1H), 3.6-3.4 (m, 2H), 3.21 (m, 4H), 3.03 (m, 2H), 2.52 (s, 6H), 2.07 (s, 3H), 2.05 (m, 2H), 1.78 (m, 2H); Mass spectrum (ESI) m/z 570.5 (100%, M+H + ).

›EXAMPLE 1198

3- 1- 3-(N-4,5-Dihydroimidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(benzyloxycarbonylamino)propionic acid trifluoroacetate

A. 1-(3-aminoproply)-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1081 Part A (4.20 g, 11.1 mmol), ethanol (75 mL), dry tetrahydrofuran (75 mL) and anhydrous hydrazine (1.5 mL) was stirred at room temperature for 16 h. Dry tetrahydrofuran (100 mL) was added, the mixture was filtered and the filtrate was concentrated to provide the title product, which was used directly in the subsequent reaction without purification: 1 H NMR (CDCl 3 ) δ 8.51 (s, 1H), 8.10 (s, 1H), 8.06 (d, 1H), 7.46 (d, 1H), 4.52 (t, 2H), 4.41 (q, 2H), 2.68 (t, 2H), 2.06 (m, 2H), 1.72 (bs, 2H), 1.43 (t, 3H).

B. 1- 3-(N-4,5-Dihydroimidazol-2-ylamino)propyl!-5-ethoxycarbonylindazole hydriodide

The crude product of Example 1198 Part A was combined with 2-methylthio-4,5-dihydroimidazole hydriodide (2.71 g, 11.1 mmol) and pyridine (125 mL), and the mixture was heated at 80° C. for 5 h. The mixture was allowed to cool to room temperature and concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane:methanol 80:20) to provide the title product (3.73 g, 75%) as a gum: 1 H NMR (DMSO-d 6 ) δ 8.50 (s, 1H), 8.30 (s, 1H), 8.24 (bs, 1H), 7.98 (d, 1H), 7.75 (d, 1H), 4.49 (t, 2H), 4.34 (q, 2H), 3.57 (s, 4H), 3.13 (m, 2H), 2.05 (m, 2H), 1.35 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 316.1774, found 316.1765.

C. tert-Butyl 3- 1- 3-(N-4,5-Dihydroimidazol-2yl-amino)-propyl!indazol-5-ylcarbonylamino!-2(S)-(benzyloxycarbonylamino)propionate hydrochloride

A mixture of the product prepared according to Example 1198 Part B (3.39 g, 7.64 mmol), aqueous sodium hydroxide (1.0M; 16 mL, 16 mmol) and ethanol (35 mL) was stirred at reflux for 16 h. The mixture was allowed to cool to room temperature and was treated with aqueous hydrochloric acid (1.0M; 16 mL, 16 mmol). The solvent was evaporated under vacuum, benzene was added and solvent was again evaporated. A portion of the resulting residue (77 mg, 240 μmol) was combined with tert-butyl 3-amino-2(S)-benzyloxycarbonylamino)propionate (prepared according to Mokotoff and Logue, J. Med. Chem. 1981, 24, 554; 70 mg, 240 μmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (60 mg, 313 μmol), 1-hydroxybenzotriazole hydrate (10 mg), dry N,N-dimethylformamide (5 mL) and triethylamine (0.1 mL), and the resulting mixture was stirred at room temperature for 16 h. The mixture was concentrated under vacuum and benzene (20 mL) was added. The solvent was evaporated and the residue was purified by flash chromatography (dichloromethane:methanol 90:10) to provide the title product (122 mg, 85%) as a yellow gum: 1 H NMR (DMSO-d 6 ) δ 8.53 (bt, 1H), 8.30 (s, 1H), 8.24 (s+m, 2H), 7.88 (d, 1H), 7.71 (d, 1H), 7.70 (m, 1H), 7.34 (m, 5H), 5.04 (s, 2H), 4.47 (t, 2H), 4.23 (m, 1H), 3.75-3.50 (m, 2H), 3.55 (s, 4H), 3.12 (q, 2H), 2.06 (m, 2H), 1.33 (s, 9H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 564.2934, found 564.2959.

D. 3- 1- 3-(N-4,5-Dihydroimidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino)-2(S)-(benzyloxycarbonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1081 Part H, the product prepared according to Example 1198 Part C (108 mg, 180 μmol) was converted to the title product (74 mg, 75%) as a hygroscopic, off-white solid: 1 H NMR (DMSO-d 6 ) δ 8.57 (bt, 1H), 8.31 (s, 1H), 8.28 (m, 1H), 8.24 (s, 1H), 7.88 (d, 1H), 7.72 (d, 1H), 7.62 (m, 1H), 7.32 (m, 5H), 5.02 (s, 2H), 4.47 (t, 2H), 4.29 (m, 1H), 3.65 (m, 2H), 3.55 (s, 4H), 3.11 (q, 2H), 2.06 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 508.2308, found 508.2323.

›EXAMPLE 1213

3- 1- 3-(N-4,5-Dihydroimidazol-2-ylamino)-propyl!indazol-5-ylcarbonylamino!-2(S)-(benzenesulfonylamino)propionic acid trifluoroacetate

A. tert-Butyl 3- 1- 3-(N-4,5-dihydroimidazol-2yl-amino)propyl!indazol-5-ylcarbonylamino!-2(S)-(benzenesulfonylamino)propionate hydrochloride

A mixture of tert-butyl 3-benzyloxycarbonylamino-2-(S)-benzenesulfonylamino)propionate (200 mg, 460 μmol), methanol (15 mL) and 10% palladium on charcoal (25 mg) was stirred at room temperature. Hydrogen gas was bubbled through the solution for 5 minutes, and a hydrogen-filled balloon was then placed on the reaction flask. The mixture was stirred at room temperature for 3 h, then was filtered through Celite®. The solids were washed with methanol and the filtrate was concentrated. The residue was mixed with a portion of the intermediate residue obtained in Example 1198 Part C (149 mg, 460 μmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (120 mg, 626 μmol), 1-hydroxybenzotriazole hydrate (20 mg), dry N,N-dimethylformamide (10 mL) and triethylamine (0.2 mL). The mixture was stirred at room temperature for 16 h. The solvent was removed under vacuum and the residue was purified by flash chromatography (dichloromethane:ethanol 75:25) to provide the title product (220 mg, 78%) as a gum: 1 H NMR (CDCl 3 ) δ 8.66-7.04 (m, 13H), 5.99 (bs, 1H), 4.52-1.98 (m, 15H), 1.30 (s, 9H); High resolution mass spectrum calculated (M+H + ) 570.2499, found 570.2503.

B. 3- 1- 3-(N-4,5-Dihydroimidazol-2-ylamino)propyl!-indazol-5-ylcarbonylamino!-2(S)-(benzenesulfonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1081 Part H, the product prepared according to Example 1213 Part A (202 mg, 333 μmol) was converted to the title product (151 mg, 82%) as a hygroscopic solid: 1 H NMR (DMSO-d 6 ) δ 8.56-7.08 (m, 15H), 4.54-2.01 (m, 13H); High resolution mass spectrum calculated (M+H + ) 514.1873, found 514.1879.

›EXAMPLE 1216b

3- 1- 3-(N-4,5-Dihydroimidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

A. tert-Butyl 3- 1- 3-(N-4,5-dihydroimidazol-2-yl-amino)propyl!indazol-5-ylcarbonylamino-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionate hydriodide

A mixture of the product prepared according to Example 1178b Part G (60 mg, 110 μmol), 2-methylthioimidazoline hydriodide (32 mg, 130 μmol) and pyridine (5 mL) was heated on an oil bath at 120° C. After 16 h, the mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane:methanol, step gradient from 98:2 to 90:10) to provide the title product (30 mg, 37%): 1 H NMR (CDCl 3 ) δ 8.03 (s, 1H), 7.82 (s, 1H), 7.73 (d, 1H), 7.70 (bm, 1H), 7.31 (d, 1H), 6.84 (s, 1H), 4.39 (m, 2H), 3.99 (m, 1H), 3.78 (m, 2H), 3.48 (s, 4H), 3.01 (m, 2H), 2.60 (s, 6H), 2.21 (m, 2H), 2.17 (s, 3H), 1.24 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 612.2968, found 612.2975.

B. 3- 1- 3-(N-4,5-Dihydroimidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1129 Part H, followed by purification by preparative reverse phase high pressure liquid chromatography (acetonitrile:water containing 0.05% trifluoroacetic acid; gradient from 10:90 to 90:10), the product prepared according to Example 1216b Part A was converted to the title product (15 mg, 48%): 1 H NMR (MeOH-d 4 ) δ 8.16 (s, 2H), 7.79 (d, 1H), 7.59 (d, 1H), 6.76 (s, 2H), 4.52 (t, 2H), 4.16 (dd, 1H), 3.77 (dd, 1H), 3.59 (s, 4H), 3.47 (dd, 1H), 3.16 (m, 2H), 2.57 (s, 6H), 2.18 (m, 2H), 2.02 (s, 3H); High resolution mass spectrum (FAB) calculated (M+H + ) 556.2372, found 556.2342.

›EXAMPLE 1326b

3- 1- 1-(RS)-Methyl-3-(N-pyridin-2ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

A. 1-(1-(RS)-methyl-2-cyanoethyl)-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1050e Part C (1.90 g, 10 mmol), crotononitrile (4.9 mL, 60 mmol), sodium bis(trimethylsilyl)amide (1.0M in tetrahydrofuran; 0.5 mL, 0.5 mmol) and ethanol (20 mL) was heated at reflux for 18 h. The solution was cooled to room temperature and treated with aqueous hydrochloric acid (1.0M; 0.5 mL). The solvent was removed under vacuum, and the residue was taken up in dichloromethane and washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate 60:40) to provide the title product (2.49 g, 96%) as a viscous syrup which gradually solidified on standing: 1 H NMR (CDCl 3 ) δ 8.53 (s, 1H), 8.17 (s, 1H), 8.11 (d, 1H), 7.45 (d, 1H), 5.03 (m, 1H), 4.41 (q, 2H), 3.05 (m, 2H), 1.74 (d, 3H), 1.43 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 258.1243, found 258.1248.

B. 1-(1-(RS)-methyl-3-aminopropyl)-5-ethoxycarbonylindazole hydrochloride

Using the procedure of Example 1129 Part B, the product prepared according to Example 1326b Part A (2.0 g, 7.8 mmol) was converted into the title product (2.22 g, 96%) as a pale yellow, hygroscopic glass: 1 H NMR (DMSO-d 6 ) δ 8.48 (s, 1H), 8.33 (s, 1H), 8.10 (bs, 3H), 7.96 (d, 1H), 7.88 (d, 1H), 5.11 (m, 1H), 4.34 (q, 2H), 2.75 (bm, 1H), 2.45 (bm, 1H), 2.30 (bm, 1H), 2.15 (bm, 1H), 1.49 (d, 3H), 1.35 (t, 3H); high resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 262.1556, found 262.1561.

C. 1-(1-(RS)-methyl-3- N-(1-oxido)pyridin-2-ylamino!propyl)-5-ethoxycarbonylindazole. Using the procedure of Example 1081 Part C, the product prepared according to Example 1326b Part B (596 mg, 2.0 mmol) was converted into the title product (312 mg, 44%) as a tan glass: 1 H NMR (CDCl 3 ) δ 8.52 (s, 1H), 8.18 (s, 1H), 8.09 (d, 1H), 7.98 (d, 1H), 7.38 (d, 1H), 6.99 (t, 1H), 6.82 (bt, 1H), 6.51 (d, 1H), 4.90 (m, 1H), 4.41 (q, 2H), 3.12 (m, 1H), 2.95 (m, 1H), 2.61 (m, 1H), 2.22 (m, 1H), 1.62 (d, 3H), 1.42 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 355.1770, found 355.1771.

D. 1-(1-(RS)-methyl-3- N-pyridin-2-ylamino!propyl)-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1326b Part C (292 mg, 824 μmol), polymer-supported triphenylphosphine (550 mg, ca. 1.65 mmol) and N,N-dimethylformamide (5 mL) was heated on an oil bath at 160° C. After 18.5 h, an additional aliquot of polymer-supported triphenylphosphine (550 mg) was added, and the reaction was heated for 24 h more. The mixture was cooled to room temperature and filtered. The solid was washed with N,N-dimethylformamide, and the filtrate was concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane:methanol 96:4) and rotary thin-layer chromatography (dichloromethane:methanol 97:3) to provide the title product (189 mg, 67%) as a pale yellow gum which gradually solidified on standing: 1 H NMR (CDCl 3 ) δ 8.52 (s, 1H), 8.16 (s, 1H), 8.05-8.00 (m, 2H), 7.41 (d, 1H), 7.33 (t, 1H), 6.54 (t, 1H), 6.19 (d, 1H), 4.87 (m, 1H), 4.50-4.30 (m, 3H), 3.16 (m, 1H), 3.05 (m, 1H), 2.45 (m, 1H), 2.23 (m, 1H), 1.61 (d, 3H), 1.42 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 339.1821, found 339.1832.

E. 1-(1-(RS)-methyl-3- N-pyridin-2-ylamino!propyl)-5-carboxyindazole

A mixture of the product prepared according to Example 1326b Part D (180 mg, 532 μmol), aqueous sodium hydroxide (1.0M; 2.13 mL, 2.13 mmol) and ethanol (4 mL) was heated to reflux. After 4.25 h, the solution was cooled to room temperature and concentrated under vacuum. The residue was used directly in the next reaction without purification or characterization.

F. tert-Butyl 3- 1- 1-(RS)-methyl-3-(N-pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(S)-(2,4,6-trimethylbenzenesulfonylamino)propionate

The product of Example 1326b Part E was combined with the product prepared according to Example 1178b Part E (183 mg, 535 μmol), 1-hydroxybenzotriazole hydrate (72 mg, 535 μmol), N,N-dimethylformamide (8 mL), and triethylamine (1 drop), and the mixture was treated with dicyclohexylcarbodiimide (121 mg, 589 μmol) and stirred at room temperature. After 21.75 h, the mixture was diluted with ethyl acetate and filtered. The filtrate was concentrated under vacuum, and the residue was purified by flash chromatography (dichloromethane:methanol 97:3) to provide the title product (286 mg, 85%) as a colorless glass: 1 H NMR (CDCl 3 ) δ 8.21 (s, 1H), 8.12 (s, 1H), 8.04 (dd, 1H), 7.77 (dt, 1H), 7.40 (d, 1H), 7.33 (t, 1H), 6.93 (s, 2H), 6.87 (bt, 1H), 6.53 (dd, 1H), 6.18 (d, 1H), 6.01 (bs, 1H), 4.86 (bm, 1H), 4.51 (m, 1H), 4.0-3.8 (m, 2H), 3.65 (m, 1H), 3.15 (m, 1H), 3.03 (m, 1H), 2.66 (s, 6H), 2.44 (m, 1H), 2.26 (s, 3H), 2.22 (m, 1H) 1.61 (d, 3H), 1.30 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 635.3016, found 635.3019.

G. 3- 1- 1-(RS)-Methyl-3-(N-pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonyl)aminopropionic acid trifluoroacetate

Using the procedure of Example 1129 Part H, the product prepared according to Example 1326b Part F (109 mg, 172 μmol) was converted to the title product (92 mg, 77%) as a white powder: 1 H NMR (DMSO-d 6 ) δ 8.43 (bt, 2H), 8.27 (s, 1H), 8.17 (s, 1H), 8.06 (d, 1H), 7.8-7.6 (m, 4H), 6.87 (d, 1H), 6.82 (d, 2H), 6.74 (t, 1H), 5.02 (m, 1H), 4.02 (q, 1H), 3.57 (m, 1H), 3.40 (m, 1H), 3.07 (m, 2H), 2.53 (s, 6H), 2.37 (m, 1H), 2.21 (m, 1H), 2.05 (s, 3H), 1.52 (d, 3H); High resolution mass spectrum (FAB) calculated (M+H + ) 579.2390, found 579.2405.

›EXAMPLE 1326f

3- 1- 3-(N-pyridin-2ylamino)propyl!-3-phenylindazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

A. 3-Bromo-5-ethoxycarbonylindazole

A solution of the product prepared according to Example 1050e Part C (3.80 g, 20 mmol) in acetic acid (120 mL) was stirred at room temperature and treated with bromine (1.55 mL, 30 mmol). The mixture was stirred in the dark for 51 h, then was poured into water (600 mL). The resulting slurry was stirred at room temperature and treated with small portions of solid sodium bisulfite, whereupon the original orange color faded to almost white. After stirring 20 min more, the solid was collected by filtration, rinsed with water and dried to provide the title product (5.14 g, 96%) as a white solid. While pure enough for use in subsequent reactions, this material could be purified further by flash chromatography (hexanes:ethyl acetate 70:30): 1 H NMR (DMSO-d 6 ) δ 13.80 (bs, 1H), 8.20 (d, 1H), 8.01 (dd, 1H), 7.69 (d, 1H), 4.36 (q, 2H), 1.37 (t, 3H); Mass spectrum (NH 3 --CI) m/z 269 (100%), 271 (95%) (M+H + ).

B. 3-Phenyl-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1326f Part A (2.69 g, 10.0 mmol), phenylboronic acid (1.71 g, 14.0 mmol), triethylamine (5.6 mL, 40.0 mmol), and N,N-dimethylformamide (20 mL) was purged of oxygen by bubbling with nitrogen for 20 min. Tetrakis(triphenylphosphine)palladium (580 mg, 500 μmol) was added, and the mixture was heated on an oil bath at 110° C. under nitrogen. After 48 h, the mixture was cooled to room temperature and diluted with water. The mixture was extracted with ethyl acetate, and the organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate 80:20) to provide the title product (542 mg, 20 %) as a white solid: 1 H NMR (CDCl 3 ) δ 11.44 (bs, 1H), 8.78 (s, 1H), 8.06 (d, 1H), 8.01 (d, 2H), 7.57 (t, 2H), 7.49 (t, 1H), 7.30 (d, 1H), 4.44 (q, 2H), 1.43 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 267.1134, found 267.1132.

C. 1-(2-Cyanoethyl)-3-phenyl-5-ethoxycarbonylindazole

Using the procedure of Example 1129 Part A, followed by purification by flash chromatography (hexanes:ethyl acetate 70:30),the product prepared according to Example 1326f Part B (266 mg, 1.0 mmol) was converted to the title product (263 mg, 82%) as a white solid: mp 99°-102° C.; 1 H NMR (CDCl 3 ) δ 8.77 (s, 1H), 8.16 (d, 1H), 7.96 (m, 2H), 7.60-7.40 (m, 4H), 4.73 (t, 2H), 4.43 (q, 2H), 3.10 (t, 2H), 1.44 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 320.1399, found 320.1386.

D. 1-(3-aminopropyl)-3-phenyl-5-ethoxycarbonylindazole hydrochloride

Using the procedure of Example 1129 Part B, the product prepared according to Example 1326f Part C (214 mg, 670 μmol) was converted to the title product (260 mg, >100%) as a tan solid which was not purified, but was used directly in subsequent reactions: 1 H NMR (DMSO-d 6 ) δ 8.64 (s, 1H), 8.05 (d, 1H), 8.0-7.9 (m), 7.60 (t, 2H), 7.49 (m, 1H), 4.63 (t, 2H), 4.37 (q, 2H), 2.90 (m, 2H), 2.18 (m, 2H), 1.36 (t, 3H); High resolution mass spectrum (ESI) calculated (M+H + ) 323.1634, found 323.1645.

E. 1- 3-(N-(1-oxido)pyridin-2-ylamino)propyl!-3phenyl-5-ethoxycarbonylindazole

Using the procedure of Example 1081 Part C, the crude product of Example 1326f Part D was converted into the title product (122 mg, 43%) as a tan glass: 1 H NMR (CDCl 3 ) δ 8.78 (s, 1H), 8.13 (d, 1H), 8.07 (d, 1H), 7.99 (d, 2H), 7.55 (t, 2H), 7.47 (d, 1H), 7.42 (d, 1H), 7.09 (t, 1H), 6.97 (bt, 1H), 6.56 (t, 1H), 6.47 (d, 1H), 4.59 (t, 2H), 4.43 (q, 2H), 3.32 (q, 2H), 2.41 (m, 2H), 1.43 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 417.1927, found 417.1918.

F. 1- 3-(N-pyridin-2-ylamino)propyl!-3-phenyl-5-ethoxycarbonylindazole

Using the procedure of Example 1129 Part F, the product prepared according to Example 1326f Part E (106 mg, 255 μmol) was converted to the title product (39 mg, 38%) as a glass: 1 HNMR (CDCl 3 ) δ 8.77 (s, 1H), 8.08 (m, 2H), 7.98 (d, 2H), 7.54 (t, 2H), 7.5-7.3 (m, 3H), 6.56 (t, 1H), 6.32 (d, 1H), 4.77 (bt, 1H), 4.55 (t, 2H), 4.42 (q, 2H), 3.35 (q, 2H), 2.30 (m, 2H), 1.43 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 401.1978, found 401.1977.

G. tert-Butyl 3- 1- 3-(N-pyridin-2-ylamino)propyl!-3-phenylindazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionate

Using the procedures of Example 1326b Parts E and F, the product prepared according to Example 1326f Part F (38 mg, 95 μmol) was converted to the title product (59 mg, 89%) as a glass: 1 H NMR (CDCl 3 ) δ 8.57 (s, 1H), 8.08 (d, 1H), 8.01 (d, 2H), 7.85 (d, 1H), 7.53 (t, 2H), 7.5-7.4 (m, 3H), 6.97 (m, 1H), 6.92 (s, 2H), 6.57 (dd, 1H), 6.33 (d, 1H), 5.86 (d, 1H), 4.57 (t, 2H), 3.98 (m, 1H), 3.83 (m, 1H), 3.53 (m, 1H), 3.35 (q, 2H), 2.65 (s, 6H), 2.31 (m, 2H), 2.24 (s, 3H), 1.31 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 697.3172, found 692.3184.

H. 3- 1- 3-(N-pyridin-2-yl)aminopropyl!3-phenylindazol-5-yl!carbonylamino-2(S)-(2,4,6-trimethylbenzenesulfonyl)aminopropionic acid trifluoroacetate

Using the procedure of Example 1129 Part H. the product prepared according to Example 1326f Part G (44 mg, 63 μmol) was converted to the title product (32 mg, 80%) as an off-white powder: 1 H NMR (DMSO-d 6 ) δ 8.61 (bt, 1H), 8.38 (s, 1H), 8.08 (d, 1H), 8.01 (d, 2H), 7.88 (d, 1H), 7.82 (d, 1H), 7.75 (d, 1H), 7.71 (bm, 1H), 7.57 (t, 2H), 7.47 (t, 1H), 6.86 (bd, 1H), 6.72 (bt, 1H), 6.70 (s, 2H), 4.61 (t, 2H), 4.07 (in, 1H), 3.58 (m, 1H), 3.5-3.3 (m, 3H), 2.51 (s, 6H), 2.23 (in, 2H), 1.92 (s, 3H); High resolution mass spectrum (FAB) calculated (M+H + ) 641.2546, found 641.2569.

›EXAMPLE 1326g

3- 1- 3-(N-pyridin-2-ylamino)propyl!-3-(2-phenylethyl)indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

A. 3-Phenylethynyl-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1326f Part A (269 mg, 1.0 mmol), triphenylphosphine (21 mg, 80 μmol), copper(I) iodide (8 mg, 40 μmol), phenylacetylene (165 μL, 1.5 mmol) and diethylamine (5 mL) was purged of oxygen by bubbling with nitrogen for 35 min. Bis(triphenylphosphine)palladium(II) chloride (14 mg, 20 μmol) was then added, and the mixture was heated to reflux under nitrogen. After 16.5 h, the mixture was cooled to room temperature and concentrated under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate 80:20) to provide the title product (227 mg, 78%) as a yellowish solid: 1 H NMR (CDCl 3 ) δ 8.66 (s, 1H), 8.13 (d, 1H), 7.68 (m, 2H), 7.55 (d, 1H), 7.42 (m, 3H), 4.45 (q, 2H), 1.45 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 291.1134, found 291.1111.

B. 1-(2-Cyanoethyl)-3-(2-phenylethynyl)-5-ethoxycarbonylindazole

Using the procedure of Example 1129 Part A, the product prepared according to Example 1326g Part A (278 mg, 958 μmol) was converted to the title product (254 mg, 77%) as a tan solid: mp 90°-94° C.; 1 H NMR (CDCl 3 ) δ 8.63 (s, 1H), 8.17 (d, 1H), 7.67 (m, 2H), 7.52 (d, 1H), 7.42 (m, 3H), 4.70 (t, 2H), 4.45 (q, 2H), 3.09 (t, 2H), 1.46 (t, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 344.1399, found 344.1391.

C. 1-(3-Aminopropyl)-3-(2-phenylethyl)-5-ethoxycarbonylindazole hydrochloride

Using the procedure of Example 1129 Part B. the product prepared according to Example 1326g Part B (240 mg, 699 μmol) was converted to the title product (277 mg, >100%) as a pale yellow solid which was not purified, but was used directly in subsequent reactions: 1 H NMR (DMSO-d 6 ) δ 4.50 (m, 2H), 3.28 (t, 2H), 3.05 (t, 2H), 2.80 (m, 2H), 2.10 (m, 2H).

D. 1- 3- N-(1-oxido)pyridin-2-ylamino!propyl!-3-(2-phenylethyl)-5-ethoxycarbonylindazole

Using the procedure of Example 1081 Part C, the crude product of Example 1326g Part C was converted into the title product (145 mg, 46%) as a pale yellow glass which was not purified but was used in subsequent reactions: Mass spectrum (ESI) m/z 445.4 (100%, M+H + ).

E. 1- 3- N-pyridin-2-ylamino!propyl!-3-(2phenylethyl)-5-ethoxycarbonylindazole

Using the procedure of Example 1326b Part D, the impure product of Example 1326g Part D was converted to the title product (90 mg, 70%) as a yellow gum, which impure but was used in subsequent reactions without further purification.

F. tert-Butyl 3- 1- 3-(N-pyridin-2-ylamino)propyl!-3-(2-phenylethyl)indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionate

Using the procedures of Example 1326b Parts E and F, the impure product of Example 1326g Part E was converted to the title product (98 mg, 64%) as a glass, which was impure but was used without further purification in the subsequent reaction.

G. 3- 1- 3-(N-pyridin-2-ylamino)propyl!-3-(2phenylethyl)indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1129 Part H, the impure product of Example 1326g Part F was converted to the title product. The crude material was purified by preparative reverse-phase high pressure liquid chromatography (acetonitrile-water containing 0.05% trifluoroacetic acid, gradient from 10:90 to 90:10) to provide the title product (20 mg, 20 %) as an off-white powder: High resolution mass spectrum (FAB) calculated (M+H + ) 669.2859, found 669.2881.

›EXAMPLE 1327b

3- 1- 2-(N-Imidazol-2-ylaminocarbonyl)ethyl!indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

A. 1-(2-tert-Butyloxycarbonylethyl)-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1050e Part C (2.0 g, 10.5 mmol), tert-butyl acrylate (9.3 mL, 63.5 mmol) and ethanol (21 mL) was treated with sodium bis(trimethylsilyl)amide (1.0M in tetrahydrofuran; 530 μL, 530 μmol). The resulting solution was heated at reflux for 3 h, then was cooled to room temperature. Aqueous hydrochloric acid (1.0M; 550 μL, 550 μmol) was added, and the mixture was concentrated. The residue was partitioned between ether and water, and the aqueous phase was extracted further with ether. The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate 85:15) to provide the title product (830 mg, 25%): 1 H NMR (CDCl 3 ) δ 8.49 (s, 1H), 8.10 (s, 1H), 8.07 (d, 1H), 7.50 (d, 1H), 4.64 (t, 2H), 4.41 (q, 2H), 2.91 (t, 2H), 1.42 (t, 3H), 1.33 (s, 9H); high resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 319.1658, found 319.1655.

B. 1-(2-Carboxyethyl)-5-ethoxycarbonylindazole

A solution of the product prepared according to Example 1327b Part A (791 mg, 2.49 mmol) in dichloromethane (28 mL) was treated with trifluoroacetic acid (6 mL). The mixture was stirred at room temperature for 16 h, then was concentrated under vacuum. Addition of ether to the residue produced, after filtering and drying, the title product (571 mg, 88%) as a white solid: 1 H NMR (CDCl 3 ) δ 8.52 (s, 1H), 8.12 (s, 1H), 8.09 (d, 1H), 7.49 (d, 1H), 4.67 (t, 2H), 4.41 (q, 2H), 3.07 (t, 2H), 1.42 (t, 3H); Mass spectrum (ESI) m/z 263.3 (100%, M+H + ).

C. 1-(2-(N-imidazol-2-ylaminocarbonyl)ethyl)-5-ethoxycarbonylindazole

A mixture of the product prepared according to Example 1327b Part B (352 mg, 1.34 mmol), 2-aminoimidazole sulfate (0.55 g, 4.15 mmol), diisopropylethylamine (1.17 mL, 6.7 mL) and N,N-dimethylformamide (7 mL) was treated with benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphonate (BOP Reagent; 891 mg, 2.0 mmol) and warmed to 70° C. on an oil bath. The mixture was stirred at this temperature for 18 h, then was cooled to room temperature and diluted with water (75 mL). The resulting precipitate was collected by filtration to provide the title product (310 mg, 71%) which was used in subsequent reactions without further purification: 1 H NMR (CDCl 3 ) δ 8.49 (s, 1H), 8.11 (s, 1H), 8.07 (d, 1H), 7.88 (b, 1H), 7.55 (d, 1H), 7.40 (b, 1H), 4.75 (t, 2H), 4.41 (q, 2H), 3.01 (t, 2H), 1.42 (t, 3H); high resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 328.1046, found 328.1031.

D. 1-(2-(N-imidazol-2-ylaminocarbonyl)ethyl)-5-carboxyindazole

A mixture of the product of Example 1327b Part C (145 mg, 443 μmol), tetrahydrofuran (2 mL) and water (2 mL) was treated with aqueous lithium hydroxide (1.0 M; 0.56 mL, 560 μmol) and stirred at room temperature for 21 h. The reaction was incomplete by thin-layer chromatography, so additional lithium hydroxide solution (a total of 1.35 mL) was added in four portions over the next 8 h. After stirring for 16 h more, the reaction was acidified with aqueous hydrochloric acid (1.0M) and concentrated under vacuum. The residue was partitioned between water and dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to provide the title product (49 mg, 37%): 1 H NMR (DMSO-d 6 ) δ 8.41 (s, 1H), 8.24 (s, 1H), 7.94 (d, 1H), 7.76 (d, 1H), 6.67 (s, 2H), 4.73 (t, 2H), 3.00 (t, 2H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 300.1097, found 300.1097.

E. tert-Butyl 3- 1- 2-(N-imidazol-2ylaminocarbonyl)ethyl!indazol-5-ylcarbonylamino!-2-(S)-(2,4,6-trimethylbenzenesulfonylamino)propionate

Using the procedure of Example 1326b Part F, the product prepared according to Example 1327b Part D (48 mg, 160 μmol) was converted to the title product (32 mg, 32%): Mass spectrum (ESI) m/z 624.4 (100%, M+H + ).

F. 3- 1- 2-(N-imidazol-2-ylaminocarbonyl)ethyl!indazol-5-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1081 Part H followed by purification by preparative reverse phase high pressure liquid chromatography (acetonitrile:water containing 0.05% trifluoroacetic acid, gradient from 10:90 to 90:10), the product prepared according to Example 1327b Part E (32 mg, 52 μmol) was converted to the title product (28 mg, 95%) as a white powder after lyophilization: 1 H NMR (MeOH-d 4 ) δ 8.11 (s, 1H), 8.09 (s, 1H), 7.77 (d, 1H), 7.68 (d, 1H), 7.10 (s, 2H), 6.73 (s, 2H), 4.81 (t, 2H), 4.14 (dd, 1H), 3.75 (dd, 1H), 3.47 (dd, 1H), 3.19 (t, 1H), 2.56 (s, 6H), 1.97 (s, 3H); high resolution mass spectrum (FAB) calculated (M+H + ) 568.1978, found 568.1972.

›EXAMPLE 2328

3- 1- 4-(N-4,5-Dihydroimidazol-2-ylamino)butyl!indazol-4-ylcarbonylamino!-2(S)-(benzyloxycarbonylamino)propionic acid trifluoroacetate

A. Methyl 2-methyl-3-aminobenzoate

A mixture of methyl 2-methyl-3-nitrobenzoate (30 g, 154 mmol), 10% palladium on charcoal (3.0 g) and ethanol (350 mL) was shaken under hydrogen at 50 psig. After 4 h, the mixture was filtered through Celite® and the solids were washed with additional ethanol. The filtrate was concentrated to provide the title product (24.4 g, 96%) as a tan oil: 1 H NMR (CDCl 3 ) δ 7.18 (m, 1H), 7.06 (m, 1H), 6.78 (m, 1H), 3.85 (s, 3H), 2.34 (s, 3H); high resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 166.0868, found 166.0866.

B. 4-Methoxycarbonylindazole

The product prepared according to Example 2328 Part A (24.25 g, 147 mmol) was combined with concentrated hydrochloric acid (30.1 mL) and water (170 mL). Ammonium tetrafluoroborate (20.62 g, 197 mmol) was added and the mixture was stirred at 0° C. A solution of sodium nitrite (10.14 g, 147 mmol) in water (25 mL) was added dropwise, and the mixture was stirred for 40 min after addition was complete. The white precipitate was collected by filtration and washed with water (3×80 mL), then with methanol (80 mL) and finally with ether (3×60 mL). The resulting solid was added to a stirred mixture of potassium acetate (17.89 g, 182 mmol), 18-crown-6 (1.20 g, 4.5 mmol) and chloroform (360 mL) at room temperature. The resulting mixture was stirred for 50 min, then water (250 mL) was added and the layers were separated. The organic phase was washed with water (250 mL) and brine (300 mL), and drIed over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with hexanes and filtered to provide after drying the title product (16.96 g, 62%) as an orange solid: 1 H NMR (CDCl 3 ) δ 8.60 (s, 1H), 7.98 (d, 1H), 7.74 (d, 1H), 7.42 (t, 1H), 4.01 (s, 3H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 177.0664, found 177.0669.

C. 1- 4-(N-phthalimido)butyl!-4-methoxycarbonylindazole

Following the procedure of Example 1081 Part A, the product prepared according to Example 2328 Part B (2.97 g, 16.9 mmol) and N-(4-bromobutyl)phthalimide (4.99 g, 16.9 mmol) were converted to the title product (1.88 g, 29%) as an orange oil: 1 H NMR (CDCl 3 ) δ 8.45 (s, 1H), 7.91 (d, 1H), 7.82 (m, 2H), 7.72 (m, 2H), 7.66 (d, 1H), 7.43 (t, 1H), 4.46 (t, 2H), 4.02 (t, 3H), 3.75 (t, 2H), 1.99 (m, 2H), 1.72 (m, 2H); Mass spectrum (NH 3 --CI) m/z 378.0 (100%, M+H + ).

D. 1- 4-(Aminobutyl)-4-methoxycarbonylindazole

Using the procedure of Example 1081 Part B, the product prepared according to Example 2328 Part C (1.81 g, 4.8 mmol) was converted to the title product (0.72 g, 60%) as a yellow oil: 1 H NMR (CDCl 3 ) δ 8.48 (s, 1H), 7.93 (d, 1H), 7.64 (d, 1H), 7.44 (t, 1H), 4.44 (t, 2H), 4.02 (s, 3H), 2.74 (t, 2H), 2.00 (m, 2H), 1.84 (bs, 2H), 1.47 (m, 2H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ); 248.1399, found 248.1391.

E. 1- 4-(N-4,5-Dihydroimidazol-2ylamino)butyl!-4-methoxycarbonylindazole hydriodide

Using the procedure of Example 1198 Part B, the product prepared according to Example 2328 Part D (247 mg, 1.0 mmol) was converted to the title product (223 mg, 50%) as a gum. 1 H NMR (DMSO-d 6 ) δ 8.37 (s, 1H), 8.11 (bs, 1H), 8.01 (d, 1H), 7.82 (d, 1H), 7.51 (t, 1H), 4.46 (t, 2H), 3.90 (s, 3H), 3.53 (s, 4H), 3.08 (m, 2H), 1.81 (m, 2H), 1.38 (m, 2H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 316.1774, found 316.1772.

F. tert-Butyl 3- 1- 4-(N-4,5-dihydroimidazol-2-yl-amino)butyl!indazol-4-ylcarbonylamino!-2(S)-(benzyloxycarbonylamino)propionate hydrochloride

Using the procedure of Example 1198 Part C, the product prepared according to Example 2328 Part E (215 mg, 485 μmol) was converted to the title product (178 mg, 59%) as a clear gum: 1 H NMR (DMSO-d 6 ) δ 8.52 (m, 1H), 8.32 (s, 1H), 8.13 (bm, 1H), 7.85 (d, 1H), 7.69 (d, 1H), 7.50 (t, 2H), 7.45 (m, 1H), 7.30 (m, 5H), 5.01 (s, 2H), 4.44 (t, 2H), 4,24 (m, 1H), 3.75-3.50 (m, 2H), 3.50 (s, 4H), 3.19 (m, 2H), 1.80 (m, 2H), 1.37 (m, 2H), 1.31 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ); 578.3091, found 578.3119.

G. 3- 1- 4-(N-4,5-Dihydroimidazol-2-ylamino)butyl!indazol-4-ylcarbonylamino!-2(S)-(benzyloxycarbonylamino)propionic acid hydrochloride

Using the procedure of Example 1081 Part H, the product prepared according to Example 2328 Part F (121 mg, 197 μmol) was converted to the title product (88 mg, 80%) as a hygroscopic white solid: 1 H NMR (DMSO-d 6 ) δ 8.57 (m, 1H), 8.31 (s, 1H), 8.18 (bm, 1H), 7.86 (d, 1H), 7.63 (d, 1H), 7.50-7.35 (m, 3H), 7.30 (m, 5H), 5.00 (s, 2H), 4.43 (t, 2H), 4,28 (m, 1H), 3.75-3.40 (m, 6H), 3.07 (m, 2H), 1.78 (m, 2H), 1.38 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ); 522.2465, found 522.2484.

›EXAMPLE 3093 · 1 of 2

3- 1-Methyl-3- 3-(N-imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2(S)-(2,6-dimethylbenzenesulfonylamino)propionic acid trifluoroacetate

A. 6-Methoxycarbonylindazol

Using the procedure of Example 2328 Part B, methyl 3amino-4-methylbenzoate (12.39 g, 75 mmol) was converted to the title product (8.85 g, 67%) which could be recrystallized from acetonitrile to give pale orange crystals: mp 142°-144° C.; 1 H NMR (CDCl 3 ) δ 11.17 (bs, 1H), 8.30 (s, 1H), 8.18 (s, 1H), 7.83 (m, 2H), 3.97 (s, 3H); Mass spectrum (NH 3 --CI) m/z 177 (100%, M+H + ).

B. 3-Bromo-6-methoxycarbonylindazole

Using the procedure of Example 1326f Part A, the product prepared according to Example 3093 Part A (3.52 g, 20 mmol) was converted to the title product (4.46 g, 87%) as a light yellow powder: mp 186°-189° C.; 1 H NMR (CDCl 3 ) δ 8.24 (s, 1H), 7.91 (d, 1H), 7.70 (d, 1H), 3.92 (s, 3H); Mass spectrum (NH 3 --CI) m/z 255 (100%), 257 (96%) (M+H + ); High resolution mass spectrum (EI) calculated (M + ) 253.9691, found 253.9694.

C. 1-Methyl-3-bromo-6-methoxycarbonylindazole

Sodium hydride (60% in mineral oil; 600 mg, 15 mmol) was placed in a dry flask under nitrogen and suspended in dry N,N-dimethylformamide (20 mL). The suspension was stirred on an ice bath and treated with a solution of the product prepared according to Example 3093 Part B (2.55 g, 10 mmol) in dry N,N-dimethylformamide (20 mL) over ca. 3 min. The resulting yellow solution was stirred for 10 min more, then was treated with iodomethane (0.7 mL, 11 mmol). The mixture was stirred at room temperature for 22.5 h, then was poured into water (ca. 600 mL). After being stirred for 10 min, the suspension was filtered, and the solid was washed with water and dried to provide the title product (2.57 g, 95%) as a yellow solid, which could be recrystallized from ethanol: mp 122°-125° C.; 1 H NMR (CDCl 3 ) δ 8.16 (s, 1H), 7.87 (d, 1H), 7.65 (d, 1H), 4.13 (s, 3H), 3.99 (s, 3H); Mass spectrum (NH 3 --CI) m/z 269 (100%), 271 (92%) (M+H + ); High resolution mass spectrum (NH 3 --CI) calculated 268.9926, found 268.9914.

D. 1-Methyl-3-(3,3diethylpropyl)-6-methoxycarbonylindazole

A mixture of the product prepared according to Example 3093 Part C (1.93 g, 7.2 mmol), 3,3-diethoxypropyne (1.65 mL, 11.5 mmol), triphenylphosphine (190 mg, 720 μmol), copper(I) iodide (68 mg, 360 μmol) and triethylamine (60 mL) was purged of oxygen by bubbling with nitrogen for 25 min. Bis(triphenylphosphine)palladium(II) chloride (126 mg, 180 μmol) was added, and the mixture was heated at 100° C. After 14 h, the mixture was concentrated under a nitrogen stream and cooled to room temperature. The residue was purified by flash chromatography (hexanes:ethyl acetate 85:15) to provide an orange, sticky solid. This was recrystallized (methanol) to provide the title product (1.26 g, 56%) as light yellow fibrous needles: mp 91°-93° C.; 1 H NMR (CDCl 3 ) δ 8.18 (s, 1H), 7.88 (d, 1H), 7.83 (d, 1H), 5.59 (s, 1H), 4.14 (s, 3H), 3.98 (s, 3H), 3.89 (m, 2H), 3.72 (m, 2H), 1.30 (t, 6H); Mass spectrum (ESI) m/z 317.4 (100%, M+H + ).

E. 1-Methyl-3-(3,3diethoxypropyl)-6-methoxycarbonylindazole

A mixture of the product prepared according to Example 3093 Part D (1.24 g, 3.92 mmol), 10% palladium, on charcoal (130 mg), methanol (40 mL) and tetrahydrofuran (60 mL) was placed in a pressure bottle and shaken under an atmosphere of hydrogen (60 psig). After 60 min, the bottle was vented and the mixture was filtered through Celite.® The solids were rinsed with methanol and tetrahydrofuran, and the filtrate was concentrated under vacuum to provide the title product (1.31 g, >100%) as a slightly cloudy oil which was not purified further: 1 H NMR (CDCl 3 ) δ 8.11 (s, 1H), 7.77 (d, 1H), 7.72 (d, 1H), 4.57 (t, 1H), 4.08 (s, 3H), 3.97 (s, 3H), 3.69 (m, 2H), 3.52 (m, 2H), 3.06 (t, 2H), 2.13 (m, 2H), 1.22 (t, 6H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 321,1814, found 321.1830.

F. 1-Methyl-3-(3-oxopropyl)-6-methoxycarbonylindazole

A mixture of the product prepared according to Example 3093 Part E (1.29 g, 4.0 mmol), acetic acid (20 mL) and water (30 mL) was heated on an oil bath at 80° C. After 30 min, the solvent was removed under vacuum, and the residue-was dissolved in ethyl acetate. The solution was washed with saturated aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to provide a light brown oil. On further concentration under vacuum, a tan solid slowly formed, which was the title product (982 mg, 98%): mp 80°-83° C.; 1 H NMR (CDCl 3 ) δ 9.92 (s, 1H), 8.11 (s, 1H), 7.79 (d, 1H), 7.71 (d, 1H), 4.07 (s, 3H), 3.98 (s, 3H), 3.31 (t, 2H), 3.03 (t, 2H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 247.1083, found 247.1077.

G. 1-Methyl-3- 3- N-(1-triphenylmethylimidazol-2yl-amino)propyl!-6-methoxycarbonylindazole

A solution of the product prepared according to Example 3093 Part F (900 mg, 3.65 mmol) and the product prepared according to Example 1050e Part I (1.19 g, 3.65 mmol) in toluene (130 mL) was heated at reflux under an empty Dean-Stark water trap. After 22.5 h, additional toluene (ca. 40 mL) was removed by distillation, and the solution was cooled to room temperature under a nitrogen atmosphere. The solution was then cooled on an ice bath and treated with sodium triacetoxyborohydride (3.09 g, 14.6 mmol) and the mixture was stirred at room temperature for 21.75 h. Water (ca. 4 mL) was added cautiously and the mixture was stirred for 15 min. Additional water (75 mL) was added, and the layers were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (toluene:ethyl acetate 50:50) to provide the title product (1.56 g, 77 %) as a pale tan glass: 1 H NMR (CDCl 3 ) δ 8.07 (s, 1H), 7.72 (d, 1H), 7.43 (d, 1H), 7.30 (m, 9H), 7.20 (m, 6H), 6.68 (d, 1H), 6.38 (d, 1H), 4.01 (s, 3H), 3.97 (s, 3H), 3.13 (q, 2H), 2.96 (t, 1H), 2.61 (t, 2H), 1.61 (m, 2H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 556.2713, found 556.2732.

›EXAMPLE 3093 · 2 of 2

H. Methyl 3-amino-2-(S)-benzoyloxycarbonyl)aminopropionate, hydrochloride salt

A suspension of 3-amino-2-(S)-N-benzyloxycarbonyl)aminopropionic acid (11.0 g, 46.2 mmol) in methanol (165 mL) was stirred on an ice/acetone bath until the internal temperature was below 0° C. Thionyl chloride (3.7 mL, 50.8 mmol) was added dropwise over 10 min. The mixture was stirred for an additional 10 min at 0° C., then for 17.25 h at room temperature. The mixture was concentrated under vacuum and the gummy residue was stirred in ether (300 mL) to provide a white solid. This was collected by filtration, rinsed with additional ether and dried to provide the title product (12.9 g, 97%) as a white powder: 1 H NMR (DMSO-d 6 ) δ 8.32 (bs, 3H), 7.94 (d, 1H), 7.37 (5H), 5.07 (s, 2H), 4.45 (m, 1H), 3.68 (s, 3H), 3.22 (m, 1H), 3.07 (m, 1H).

I. Methyl 3-(tert-butyloxycarbonylamino)-2-(benzyloxycarbonylamino)propionate

A suspension of the product prepared according to Example 3093 Part H (8.00 g, 27.7 mmol) in dichloromethane (140 mL) and saturated aqueous sodium bicarbonate (85 mL) was stirred at room temperature and treated with di-tert-butyldicarbonate (6.11 g, 28 mmol). The mixture was stirred at room temperature for 16.5 h, then filtered and the layers were separated. The aqueous layer was extracted with additional dichloromethane, and the combined organics were washed with brine, dried over magnesium sulfate, and concentrated under vacuum. The resulting viscous oil was stirred in hexane (ca. 200 mL) overnight. The resulting solid was collected by filtration, washed with hexane and dried to provide the title product (7.66 g, 78%) as a white powder: 1 H NMR (CDCl 3 ) δ 7.36 (5H), 5.80 (bd, 1H), 5.12 (s, 2H), 4.84 (b, 1H), 4.41 (b, 1H), 3.77 (s, 3H), 3.55 (b, 2H), 1.42 (s, 9H).

J. Methyl 3-(tert-butyloxycarbonylamino)-2-aminopropionate.

A solution of the product prepared according to Example 3093 Part I (7.50 g, 21.3 mmol) in ethanol (200 mL) was treated with 10% palladium on charcoal (0.75 g) and stirred under hydrogen (1 atmosphere) for 8.5 h. The mixture was filtered through Celite® and the solids were rinsed with additional ethanol. The filtrate was concentrated to provide the title product (4.65 g, 100%) as a viscous oil: 1 H NMR (CDCl 3 ) δ 5.02 (bs, 1H), 3.75 (s, 3H), 3.59 (t, 1H), 3.50 (m, 1H), 3.27 (m, 1H), 1.67 (bs, 2H), 1.44 (s, 9H).

K. Methyl 3-(tert-butyloxycarbonylamino)-2-(S)-(2,6-dimethylbenzenesulfonylamino)propionate

A solution of the product prepared according to Example 3093 Part J (6.24 g, 24.5 mmol), and diisopropylamine (6.34 g, 49 mmol) in dichloromethane (25 mL) was cooled on an ice bath. A solution of 2,6-dimethylbenzenesulfonyl chloride (prepared according to Wagenaar and Engberts, J. Royal Neth. Chem. Soc. 1982, 101(5), 91-94; 5.01 g, 24.5 mmol) in dichloromethane (75 mL) was added over 15 min. The ice bath was removed and the mixture was stirred at room temperature for 18 h. Additional dichloromethane was added and the solution was washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate, step gradient from 80:20 to 60:40) to provide the title product (7.25 g, 76%) as a colorless gum: 1 H NMR (CDCl 3 ) δ 7.29 (t, 1H), 7.14 (d, 2H), 5.78 (bd, 1H), 4.89 (bt, 1H), 3.92 (m, 1H), 3.55 (s, 3H), 3.47 (m, 2H), 2.68 (s, 6H), 1.42 (s, 9H).

L. Methyl 3-amino-2-(S)-(2,6-dimethylbenzenesulfonylamino)propionate (+)-camphorsulfonate

The product prepared according to Example 3093, Part K (7.25 g, 18.8 mmol) was dissolved in HCl/dioxane (4.0M; 50 mL) and the solution was stirred at room temperature for 18 h. The mixture was concentrated under vacuum to yield a hygroscopic solid (6.63 g) which was dissolved in tetrahydrofuran and treated with triethylamine (1.0 equiv.). The resulting solid was removed by filtration, and the filtrate was treated with (+)-camphorsulfonic acid (1.0 equiv.). The mixture was stirred at room temperature for 15 min, and the resulting solid was collected by filtration, rinsed with tetrahydrofuran, and dried to provide the title product (6.63 g, 68%) as a white solid: 1 H NMR (DMSO-d 6 ) δ 8.30 (bs, 1H), 7.94 (bs, 3H), 7.33 (t, 1H), 7.19 (d, 2H), 4.09 (bt, 1H), 3.21 (s, 3H), 3.10 (dd, 1H), 2.93 (dd, 1H), 2.83 (d, 1H), 2.64 (t, 1H), 2.56 (s, 6H), 2.34 (d, 1H), 2.20 (dm, 1H), 1.90 (m, 2H), 1.80 (d, 1H), 1.24 (dd, 2H), 1.01 (s, 3H), 0.70 (s, 3H).

M. Methyl 3- 1-methyl-3- 3-(N-(1-triphenylmethylimidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(2,6-dimethylbenzenesulfonylamino)propionate

A mixture of the product prepared according to Example 3093 Part G (1.43 g, 2.57 mmol), aqueous sodium hydroxide (1.0M; 13 mL, 13 mmol) and ethanol (32 mL) was heated at reflux. After 80 min, the mixture was cooled to room temperature and aqueous hydrochloric acid (1.0M; 13 mL, 13 mmol) was added. The mixture was concentrated under vacuum and dried. A portion of this material (which contains sodium chloride; 77 mg, 92 μmol) was combined with the product prepared according to Example 3093 Part L (52 mg, 101 μmol), 1-hydroxybenzotriazole hydrate (13 mg, 92 μmol), and triethylamine (25 μL, 184 μmol) in N,N-dimethylformamide (5 mL) and treated with dicyclohexylcarbodiimide (19 mg, 92 μmol). The mixture was stirred at room temperature for 2.5 days, then was concentrated under vacuum. The residue was partially purified by flash chromatography (dichloromethane:methanol 95:5) to provide the title product (75 mg, 100%) which was impure but was used directly in the subsequent reaction.

N. 3- 1-Methyl-3- 3-(N-imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2(S)-(2,6-dimethylbenzenesulfonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1050e Part M, the product prepared according to Example 3093 Part M (75 mg, 92 μmol) was converted to the title product as a white powder (after lyophilization): 1 H NMR (MeOH-d 4 ) δ 7.90 (s, 1H), 7.76 (d, 1H), 7.47 (d, 1H), 7.09 (m, 1H), 7.01 (m, 2H), 6.81 (s, 2H), 4.16 (m, 1H), 4.04 (s, 3H), 3.78 (dd, 1H), 3.52 (dd, 1H), 3.34 (t, 2H), 3.09 (t, 2H), 2.62 (s, 6H), 2.14 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 554.2186, found 554.2184.

›EXAMPLE 3142

3- 1-Methyl-3- 3-(N-pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

A. 1-Methyl-3- 3- N-pyridin-2-ylamino)propyl!-6-methoxycarbonylindazole

A solution of the product prepared according to Example 3093 Part F (201 mg, 816 μmol) and 2aminopyridine (154 mg, 1.63 mmol) in dichloroethane (4 mL) was stirred at room temperature and treated with sodium triacetoxyborohydride (346 mg, 1.63 mmol). After 16.5 h, the mixture was diluted with water (ca. 5 mL) and saturated aqueous sodium bicarbonate (ca. 2 mL) and stirred for 15 min. The mixture was extracted three times with dichloromethane, and the combined organic phases were dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (dichloromethane:isopropanol 95:5) to provide the title product (214 mg 81%) as a white solid: mp 101°-104° C.; 1 H NMR (CDCl 3 ) δ 8.13 (s, 1H), 8.07 (d, 1H), 7.76 (d, 1H), 7.67 (d, 1H), 7.39 (t, 1H), 6.56 (dd, 1H), 6.36 (d, 1H), 4.65 (bt, 1H), 4.08 (s, 3H), 3.98 (s, 3H), 3.38 (q, 2H), 3.10 (t, 3H), 2.16 (m, 2H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 325.1665, found 325.1653.

B. tert-Butyl 3- 1-methyl-3- 3-(N-pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonyl)aminopropionate

Using the procedures of Example 1326b Parts E and F, the product prepared according to Example 3142 Part A (59 mg, 182 μmol) was converted to the title product (108 mg, 93%) as a colorless glass: 1 H NMR (CDCl 3 ) δ 8.08 (d, 1H), 7.95 (s, 1H), 7.70 (d, 1H), 7.46 (d, 1H), 7.40 (m, 1H), 6.94 (s, 2H), 6.92 (m, 1H), 6.56 (m, 1H), 6.37 (d, 1H), 5.79 (d, 1H), 4.67 (m, 1H), 4.08 (s, 3H), 3.95 (m, 1H), 3.83 (m, 1H), 3.61 (m, 1H), 3.38 (q, 2H), 3.10 (t, 2H), 2.66 (s, 6H), 2.27 (s, 3H), 2.16 (m, 2H), 1.32 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 635.3016, found 635.3028.

C. 3- 1-Methyl-3- 3-(N-pyridin-2-ylamino)propyl!-indazol-6-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1129 Part H, the product prepared according to Example 3142 Part B (100 mg, 158 μmol) was converted to the title product (84 mg, 77%) as a white powder: 1 H NMR (DMSO-d 6 ) δ 8.52 (m, 2H), 8.08 (d, 1H), 7.95 (s, 1H), 7.90 (d, 1H), 7.82 (t, 1H), 7.77 (d, 1H), 7.46 (d, 1H), 6.97 (d, 1H), 6.79 (s+m, 3H), 4.05 (m, 1H), 4.01 (s, 3H), 3.59 (m, 2H), 3.39 (m, 2H), 3.03 (t, 2H), 2.52 (s, 6H), 2.07 (m, 2H), 2.00 (s, 3H); High resolution mass spectrum (FAB) calculated (M+H + ) 579.2390, found 579.2400.

›EXAMPLE 3339

3- 1-Benzyl-3- 3-(N-pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

A. 3-(3,3-Diethoxypropynyl)-6-methoxycarbonylindazole

Using the procedure of Example 3093 Part D, the product prepared according to Example 3093 Part B (2.55 g, 10 mmol) was converted to the title product (1.49 g, 49%) as a brown gum: 1 H NMR (CDCl 3 ) δ 8.28 (s, 1H), 7.90 (d, 1H), 7.85 (d, 1H), 5.61 (s, 1H), 3.98 (s, 3H), 3.88 (m, 2H), 3.75 (m, 2H), 1.31 (t, 6H); Mass spectrum (NH 3 --CI) m/z 257 (100%, (M+H-EtOH) + ).

B. 3-(3,3-Diethoxypropynyl)-6-methoxycarbonylindazole

Using the procedure of Example 3093 Part E, the product prepared according to Example 3339 Part A (263 mg, 870 μmol) was converted to the title product (106 mg, 40%) as an orange oil, which contained a contaminant but was used directly in the subsequent reaction: 1 H NMR (CDCl 3 ) δ 8.20 (s, 1H), 7.81 (d, 1H), 7.76 (d, 1H), 4.60 (t, 1H), 3.96 (s, 3H), 3.68 (m, 2H), 3.51 (m, 2H), 3.09 (m, 2H), 2.17 (m, 2H), 1.22 (t, 6H); High resolution mass spectrum (NH 3 --CI) calculated (M+H + ) 307.1658, found 307.1636.

C. 1-Benzyl-3-(3,3-diethoxypropyl)-6-methoxycarbonylindazole

A solution of the product prepared according to Example 3339 Part B (230 mg, 750 μmol) and benzyl chloride (95 μL, 826 μmol) in dry N,N-dimethylformamide (4 mL) was stirred on an ice bath and treated with sodium hydride (60% in mineral oil; 36 mg, 900 μmol).

The mixture was stirred 10 min, then was allowed to warm to room temperature and stirred for 23 h. The mixture was diluted with water and extracted three times with ethyl acetate. The combined organic phases were washed twice with water, then dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by flash chromatography (hexanes:ethyl acetate 85:15) to provide the title product (152 mg, 51%) as an oil, which was impure but was used directly in the subsequent reaction: 1 H NMR (CDCl 3 ) δ 8.08 (s, 1H), 7.75 (m, 2H), 7.25 (m, 3H), 7.17 (m, 2H), 5.59 (s, 2H), 4.56 (t, 1H), 3.94 (s, 3H), 3.67 (m, 2H), 3.50 (m, 2H), 3.08 (m, 2H), 2.2-2.05 (m, 2H), 1.22 (t, 6H); Mass spectrum (NH 3 --CI) m/z 397.5 (10%, M+H + ), 351 (100%, (M+H-EtOH) + ).

D. 1-Benzyl-3-(3-oxopropyl)-6-methoxycarbonylindazole

Using the procedure of Example 3093 Part F, the product of Example 3339 Part C (115 mg, 567 μmol) was converted to the title product (110 mg, 60%) as an oil which solidified on standing: 1 H NMR (CDCl 3 ) δ 9.91 (s, 1H), 8.08 (s, 1H), 7.78 (d, 1H), 7.72 (d, 1H), 7.27 (m, 3H), 7.16 (m, 2H), 5.57 (s, 2H), 3.93 (s, 3H), 3.33 (t, 2H), 3.05 (t, 2H); Mass spectrum (ESI) m/z 323.4 (24%, M+H + ).

E. 1-Benzyl-3- 3-(N-pyridin-2-ylamino)propyl!-6-methoxycarbonylindazole

Using the procedure of Example 3142 Part A, the product prepared according to Example 3339 Part D (91 mg, 282 μmol) was converted to the title product (90 mg, 80%) as a viscous oil which solidified on standing. This material contained a contaminant but was used directly in the subsequent reaction: 1 H NMR (CDCl 3 ) δ 8.08 (m, 2H), 7.77 (d, 1H), 7.70 (d, 1H), 7.36 (m, 1H), 7.3-7.2 (m, 3H), 7.17 (m, 2H), 6.54 (dd, 1H), 6.30 (d, 1H), 5.60 (s, 2H), 4.65 (bt, 1H), 3.93 (s, 3H), 3.37 (q, 2H), 3.13 (t, 2H), 2.16 (m, 2H); High resolution mass spectrum (FAB) calculated (M+H + ) 401.1978, found 401.1982.

F. tert-Butyl 3- 1-benzyl-3- 3-(N-pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonyl)aminopropionate

Using the procedure of Example 1326b Parts E and F, the product prepared according to Example 3339 Part E (81 mg, 202 μmol) was converted to the title product (162 mg, >100%) as a colorless glass which contained a contaminant but was used directly in the subsequent reaction: 1 H NMR (CDCl 3 ) δ 8.07 (m, 1H), 7.94 (s, 1H), 7.71 (d, 1H), 7.47 (d, 1H), 7.38 (m, 1H), 7.26 (m, 5H), 6.92 (s+bm, 3H), 6.55 (m, 1H), 6.33 (d, 1H), 5.81 (d, 1H), 5.59 (s, 2H), 4.69 (bt, 1H), 3.94 (m, 1H), 3.81 (m, 1H), 3.56 (m, 1H), 3.38 (q, 2H), 3.13 (t, 2H), 2.63 (s, 6H), 2.26 (s, 3H), 2.17 (m, 2H), 1.29 (s, 9H); High resolution mass spectrum (FAB) calculated (M+H + ) 711.3329, found 711.3341.

G. 3- 1-Benzyl-3- 3-(N-pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2(S)-(2,4,6-trimethylbenzenesulfonylamino)propionic acid trifluoroacetate

Using the procedure of Example 1129 Part H, the product prepared according to Example 3339 Part F (136 mg, 191 μmol) was converted to the title product (110 mg, 75%) as a white powder: 1 H NMR (DMSO-d 6 ) δ 8.49 (t, 1H), 8.07 (d, 1H), 8.05 (s, 1H), 7.92 (d, 1H), 7.81 (d, 1H), 7.72 (m, 1H), 7.45 (d, 1H), 7.35-17.20 (m, 5H), 6.88 (d, 1H), 6.73 (s+m, 3H), 5.62 (s, 2H), 4.05 (m, 1H), 3.58 (m, 1H), 3.5-3.3 (m, 3H), 3.05 (t, 2H), 2.52 (s, 6H), 2.07 (m, 2H), 1.95 (s, 3H); High resolution mass spectrum (FAB) calculated (M+H + ) 655.2703, found 655.2701.

Using the methods described above and modifications thereof known to one skilled in the art of organic synthesis, the following additional examples in Tables 1-8 can be prepared.

›UTILITY · 1 of 4

The compounds of Formula Ia, Ib or Ic of the present invention possess activity as antagonists of integrins such as, for example, the α v β 3 or vitronectin receptor, α v β 5 or α 5 β 1 , and as such have utility in the treatment and diagnosis of cell adhesion, angiogenic disorders, inflammation, bone degradation, cancer metastases, diabetic retinopathy, thrombosis, restenosis, macular degeneration, and other conditions mediated by cell adhesion and/or cell migration and/or angiogenesis. The integrin antagonist activity of the compounds of the present invention is demonstrated using assays which measure the binding of a specific integrin to a native ligand, for example, using the ELISA assay described below for the binding of vitronectin to the α v β 3 receptor.

The compounds of the present invention possess selectivity for the α v β 3 receptor relative to the GPIIb/IIIa receptor as demonstrated by their reduced activity in standard assays of platelet aggregation, such as the platelet aggregation assay described below.

One of the major roles of integrins in vivo is to mediate cellular interactions with adjacent cells. Cell based adhesion assays can be used to mimic these interactions in vitro. A cell based assay is more representative of the in vivo situation than an ELISA since the receptor is maintained in membranes in the native state. The compounds of the present invention have activity in cell-based assays of adhesion, for example as demonstrated in using the cell adhesion assays described below.

The compounds of Formula Ia, Ib or Ic of the present invention may be useful for the treatment or prevention of other diseases which involve cell adhesion processes, including, but not limited to, osteoporosis, rheumatoid arthritis, autoimmune disorders, bone degradation, rheumatoid arthritis, asthma, allergies, adult respiratory distress syndrome, graft versus host disease, organ transplantation, septic shock, psoriasis, eczema, contact dermatitis, osteoarthritis, atherosclerosis, metastasis, wound healing, inflammatory bowel disease and other angiogenic disorders.

The compounds of Formula Ia, Ib or Ic have the ability to suppress/inhibit angiogenesis in vivo, for example, as demonstrated using animal models of ocular neovascularization.

The compounds provided by this invention are also useful as standards and reagents in determining the ability of a potential pharmaceutical to inhibit integrin-ligand binding. These may be provided in a commercial kit comprising a compound of this invention.

As used herein "μg" denotes microgram, "mg" denotes milligram, "g" denotes gram, "μL" denotes microliter, "mL" denotes milliliter, "L" denotes liter, "nM" denotes nanomolar, "μM" denotes micromolar, "mM" denotes millimolar, "M" denotes molar and "nm" denotes nanometer. "Sigma" stands for the Sigma-Aldrich Corp. of St. Louis, Mo.

The utility of the compounds of the present invention may be assessed by testing in one or more of the following assays as described in detail below: Purified α v β 3 (human placenta)--Vitronectin ELISA, α v β 3 -Vitronectin Binding Assay, Human Aortic Smooth Muscle Cell Migration Assay, In Vivo Angiogenesis Model, Pig Restenosis Model, Mouse Retinopathy Model. A compound of the present invention is considered to be active if it has an IC 50 or K i value of less than about 10 μM for the inhibition of α v β 3 -Vitronectin Binding Assay, with compounds preferably having K i values of less than about 0.1 μM. Tested compounds of the present invention are active in the α v β 3 -Vitronectin Binding Assay.

Purified α v β 3 (human placenta)--Vitronectin ELISA

The α v β 3 receptor was isolated from human placental extracts prepared using octylglucoside. The extracts were passed over an affinity column composed of anti-α v β 3 monoclonal antibody (LM609) bound to Affigel. The column was subsequently washed extensively at pH 7 and pH 4.5 followed by elution at pH 3. The resulting sample was concentrated by wheat germ agglutinin chromatography to provide two bands by SDS gel electrophoresis which were confirmed as α v β 3 by western blotting.

Affinity purified protein was diluted at different levels and plated to 96 well plates. ELISA was performed using fixed concentration of biotinylated vitronectin (approximately 80 nM/well). This receptor preparation contains the α v β 3 with no detectable levels of α v β 5 according to the gel and according to effects of blocking antibodies for the α v β 3 or α v β 5 integrins in the ELISA.

A submaximal concentration of biotinylated vitronectin was selected based on a concentration response curve with fixed receptor concentration and variable concentrations of biotinylated vitronectin.

α v β 3 -Vitronectin Binding Assay

The purified receptor is diluted with coating buffer (20 mM Tris HCl, 150 mM NaCl, 2.0 mM CaCl 2 , 1.0 mM MgCl 2 .6H 2 O, 1.0 mM MnCl 2 .4H 2 O) and coated (100 μL/well) on Costar (3590) high capacity binding plates overnight at 4° C. The coating solution is discarded and the plates washed once with blocking/binding buffer (B/B buffer, 50 mM Tris HCl, 100 mM NaCl, 2.0 mM CaCl 2 , 1.0 mM MgCl 2 .6H 2 O, 1.0 mM MnCl 2 .4H 2 O). Receptor is then blocked (200 μL/well) with 3.5% BSA in B/B buffer for 2 hours at room temperature. After washing once with 1.0 % BSA in B/B buffer, biotinylated vitronectin (100 μL) and either inhibitor (11 μL) or B/B buffer w/1.0% BSA (11 μL) is added to each well. The plates are incubated 2 hours at room temperature. The plates are washed twice with B/B buffer and incubated 1 hour at room temperature with anti-biotin alkaline phosphatase (100 μL/well) in B/B buffer containing 1.0 % BSA. The plates are washed twice with B/B buffer and alkaline phosphatase substrate (100 μL) is added. Color is developed at room temperature. Color development is stopped by addition of 2N NaOH (25 μL/well) and absorbance is read at 405 nm. The IC 50 is the concentration of test substance needed to block 50% of the vitronectin binding to the receptor.

›UTILITY · 2 of 4

Integrin Cell-Based Adhesion Assays

In the adhesion assays, a 96 well plate was coated with the ligand (i.e., fibrinogen) and incubated overnight at 4° C. The following day, the cells were harvested, washed and loaded with a fluorescent dye. Test compounds and cells were added together and then were immediately added to the coated plate. After incubation, loose cells are removed from the plate, and the plate (with adherent cells) is counted on a fluorometer. The ability of test compounds to inhibit cell adhesion by 50% is given by the IC 50 value and represents a measure of potency of inhibition of integrin mediated binding. Compounds were tested for their ability to block cell adhesion using assays specific for α v β 3 , α v β 5 and α v β 1 integrin interactions.

Platelet Aggregation Assay

Venous blood was obtained from anesthetized mongrel dogs or from healthy human donors who were drug- and aspirin-free for at least two weeks prior to blood collection. Blood was collected into citrated Vacutainer tubes. The blood was centrifuged for 15 minutes at 150×g (850 RPM in a Sorvall RT6000 Tabletop Centrifuge with H-1000 B rotor) at room temperature, and platelet-rich plasma (PRP) was removed. The remaining blood was centrifuged for 15 minutes at 1500×g (26,780 RPM) at room temperature, and platelet-poor plasma (PPP) was removed. Samples were assayed on a PAP-4 Platelet Aggregation Profiler, using PPP as the blank (100% transmittance). 200 μL of PRP (5×10 8 platelets/mL) were added to each micro test tube, and transmittance was set to 0%. 20 μL of ADP (10 μM) was added to each tube, and the aggregation profiles were plotted (% transmittance versus time). Test agent (20 μL) was added at different concentrations prior to the addition of the platelet agonist. Results are expressed as % inhibition of agonist-induced platelet aggregation.

Human Aortic Smooth Muscle Cell Migration Assay

A method for assessing α v β 3 -mediated smooth muscle cell migration and agents which inhibit α v β 3 -mediated smooth muscle cell migration is described in Liaw et al., J. Clin. Invest. (1995) 95: 713-724).

In Vivo Angiogenesis Model

A quantitative method for assessing angiogenesis and antiangiogenic agents is described in Passaniti et al., Laboratory Investigation (1992) 67: 519-528

Pig Restenosis Model

A method for assessing restenosis and agents which inhibit restenosis is described in Schwartz et al., J. Am. College of Cardiology (1992) 19: 267-274.

Mouse Retinopathy Model

A method for assessing retinopathy and agents which inhibit retinopathy is described in Smith et al., Invest. Ophthal. & Visual Science (1994) 35: 101-111.

Dosage and Formulation

The compounds of this invention can be administered by any means that produces contact of the active agent with the agent's site of action, the α v β 3 integrin, in the body of a mammal. They can be administered by any conventional means available for use in conjunction with pharmaceuticals, either as individual therapeutic agents or in a combination of therapeutic agents, such as a antiplatelet agent such as aspirin, piroxicam, or ticlopidine which are agonist-specific, or an anti-coagulant such as warfarin or heparin, or a thrombin inhibitor such as a boropeptide, hirudin or argatroban, or a thrombolytic agent such as tissue plasminogen activator, anistreplase, urokinase or streptokinase, or combinations thereof. The compounds of the invention, or compounds of the invention in combination with other therapeutic agents, can be administered alone, but generally administered with a pharmaceutical carrier selected on the basis of the chosen route of administration and standard pharmaceutical practice.

The dosage of the novel compounds of this invention administered will, of course, vary depending upon known factors, such as the pharmacodynamic characteristics of the particular agent and its mode and route of administration; the age, health and weight of the recipient; the nature and extent of the symptoms; the kind of concurrent treatment; the frequency of treatment; and the effect desired. A daily dosage of active ingredient can be expected to be about 0.001 to 10 milligrams per kilogram of body weight.

Dosage forms (compositions suitable for administration) contain from about 0.1 milligram to about 100 milligrams of active ingredient per unit. In these pharmaceutical compositions the active ingredient will ordinarily be present in an amount of about 0.5-95% by weight based on the total weight of the composition.

The active ingredient can be administered orally in solid dosage forms, such as capsules, tablets, and powders, or in liquid dosage forms, such as elixirs, syrups, and suspensions. It can also be administered by injection, in sterile liquid dosage forms.

Gelatin capsules contain the active ingredient and powdered carriers, such as lactose, starch, cellulose derivatives, magnesium stearate, stearic acid, and the like. Similar diluents can be used to make compressed tablets. Both tablets and capsules can be manufactured as sustained release products to provide for continuous release of medication over a period of hours. Compressed tablets can be sugar coated or film coated to mask any unpleasant taste and protect the tablet from the atmosphere, or enteric coated for selective disintegration in the gastrointestinal tract.

Liquid dosage forms for oral administration can contain coloring and flavoring to increase patient acceptance.

In general, water, a suitable oil, saline, aqueous dextrose (glucose), and related sugar solutions and glycols such as propylene glycol or polyethylene glycols are suitable carriers for parenteral solutions. Solutions for parenteral administration preferably contain a water soluble salt of the active ingredient, suitable stabilizing agents, and if necessary, buffer substances. Antioxidizing agents such as sodium bisulfite, sodium sulfite, or ascorbic acid, either alone or combined, are suitable stabilizing agents. Also used are citric acid and its salts and sodium EDTA. In addition, parenteral solutions can contain preservatives, such as benzalkonium chloride, methyl- or propyl-paraben, and chlorobutanol.

›UTILITY · 3 of 4

Suitable pharmaceutical carriers are described in Remington's Pharmaceutical Sciences, Mack Publishing Company, a standard reference text in this field.

Useful pharmaceutical dosage-forms for administration of the compounds of this invention can be illustrated as follows:

Capsules

A large number of unit capsules are prepared by filling standard two-piece hard gelatin capsules each with 10 milligrams of powdered active ingredient, 150 milligrams of lactose, 50 milligrams of cellulose, and 6 milligrams magnesium stearate.

Soft Gelatin Capsules

A mixture of active ingredient in a digestable oil such as soybean oil, cottonseed oil or olive oil is prepared and injected by means of a positive displacement pump into gelatin to form soft gelatin capsules containing 10 milligrams of the active ingredient. The capsules are washed and dried.

Tablets

A large number of tablets are prepared by conventional procedures so that the dosage unit was 10 milligrams of active ingredient, 0.2 milligrams of colloidal silicon dioxide, 5 milligrams of magnesium stearate, 275 milligrams of microcrystalline cellulose, 11 milligrams of starch and 98.8 milligrams of lactose. Appropriate coatings may be applied to increase palatability or delay absorption.

The combination products of this invention, such as the novel α v β 3 antagonist compounds of this invention in combination with an anti-coagulant agent such as warfarin or heparin, or an anti-platelet agent such as aspirin, piroxicam or ticlopidine, or a thrombin inhibitor such as a boropeptide, hirudin or argatroban, or a thrombolytic agent such as tissue plasminogen activator, anistreplase, urokinase or streptokinase, or combinations thereof, can be in any dosage form, such as those described above, and can also be administered in various ways, as described above.

In a preferred embodiment, the combination products of the invention are formulated together, in a single dosage form (that is, combined together in one capsule, tablet, powder, or liquid, etc.). When the combination products are not formulated together in a single dosage form, the α v β 3 antagonist compounds of this invention and the anti-coagulant agent, anti-platelet agent, thrombin inhibitor, and/or thrombolytic agent may be administered at the same time (that is, together), or in any order, for example the compounds of this invention are administered first, followed by administration of the anti-coagulant agent, anti-platelet agent, thrombin inhibitor, and/or thrombolytic agent. When not administered at the same time, preferably the administration of the compound of this invention and any anti-coagulant agent, anti-platelet agent, thrombin inhibitor, and/or thrombolytic agent occurs less than about one hour apart, more preferably less than about 30 minutes apart, even more preferably less than about 15 minutes apart, and most preferably less than about 5 minutes apart. Preferably, administration of the combination products of the invention is oral. The terms oral agent, oral inhibitor, oral compound, or the like, as used herein, denote compounds which may be orally administered. Although it is preferable that the α v β 3 antagonist compounds of this invention and the anti-coagulant agent, anti-platelet agent, thrombin inhibitor, and/or thrombolytic agent are both administered in the same fashion (that is, for example, both orally), if desired, they may each be administered in different fashions (that is, for example, one component of the combination product may be administered orally, and another component may be administered intravenously). The dosage of the combination products of the invention may vary depending upon various factors such as the pharmacodynamic characteristics of the particular agent and its mode and route of administration, the age, health and weight of the recipient, the nature and extent of the symptoms, the kind of concurrent treatment, the frequency of treatment, and the effect desired, as described above.

As discussed above, where two or more of the foregoing therapeutic agents are combined or co-administered with the compounds of this invention, generally the amount of each component in a typical daily dosage and typical dosage form may be reduced relative to the usual dosage of the agent when administered alone, in view of the additive or synergistic effect which would be obtained as a result of addition of further agents in accordance with the present invention.

Particularly when provided as a single dosage form, the potential exists for a chemical interaction between the combined active ingredients (for example, a novel compound of this invention and an anti-coagulant such as warfarin or heparin, or a novel compound of this invention and an anti-platelet agent such as aspirin, piroxicam or ticlopidine, or a novel compound of this invention and a thrombin inhibitor such as a boropeptide, hirudin or argatroban, or a novel compound of this invention and a thrombolytic agent such as tissue plasminogen activator, anistreplase, urokinase or streptokinase, or combinations thereof). For this reason, the preferred dosage forms of the combination products of this invention are formulated such that although the active ingredients are combined in a single dosage form, the physical contact between the active ingredients is minimized (that is, reduced).

In order to minimize contact, one embodiment of this invention where the product is orally administered provides for a combination product wherein one active ingredient is enteric coated. By enteric coating one of the active ingredients, it is possible not only to minimize the contact between the combined active ingredients, but also, it is possible to control the release of one of these components in the gastrointestinal tract such that one of these components is not released in the stomach but rather is released in the intestines. Another embodiment of this invention where oral administration is desired provides for a combination product wherein one of the active ingredients is coated with a sustained-release material which effects a sustained-release throughout the gastrointestinal tract and also serves to minimize physical contact between the combined active ingredients. Furthermore, the sustained-released component can be additionally enteric coated such that the release of this component occurs only in the intestine. Still another approach would involve the formulation of a combination product in which the one component is coated with a sustained and/or enteric release polymer, and the other component is also coated with a polymer such as a low viscosity grade of hydroxypropyl methylcellulose (HPMC) or other appropriate materials as known in the art, in order to further separate the active components. The polymer coating serves to form an additional barrier to interaction with the other component.

›UTILITY · 4 of 4

Dosage forms of the combination products of the present invention wherein one active ingredient is enteric coated can be in the form of tablets such that the enteric coated component and the other active ingredient are blended together and then compressed into a tablet or such that the enteric coated component is compressed into one tablet layer and the other active ingredient is compressed into an additional layer. Optionally, in order to further separate the two layers, one or more placebo layers may be present such that the placebo layer is between the layers of active ingredients. In addition, dosage forms of the present invention can be in the form of capsules wherein one active ingredient is compressed into a tablet or in the form of a plurality of microtablets, particles, granules or non-perils, which are then enteric coated. These enteric coated microtablets, particles, granules or non-perils are then placed into a capsule or compressed into a capsule along with a granulation of the other active ingredient.

These as well as other ways of minimizing contact between the components of combination products of the present invention, whether administered in a single dosage form or administered in separate forms but at the same time by the same manner, will be readily apparent to those skilled in the art, once armed with the present disclosure.

Pharmaceutical kits useful in, for example, the inhibition of thrombus formation, the prevention of blood clots, and/or the treatment of thromboembolic disorders, which comprise a therapeutically effective amount of a compound according to the method of the present invention along with a therapeutically effective amount of an anti-coagulant agent such as warfarin or heparin, or an antiplatelet agent such as aspirin, piroxicam or ticlopidine, or a thrombin inhibitor such as a boropeptide, hirudin or argatroban, or a thrombolytic agent such as tissue plasminogen activator, anistreplase, urokinase or streptokinase, or combinations thereof, in one or more sterile containers, are also within the ambit of the present invention. Sterilization of the container may be carried out using conventional sterilization methodology well known to those skilled in the art. The sterile containers of materials may comprise separate containers, or one or more multi-part containers, as exemplified by the UNIVIALTM™ two-part container (available from Abbott Labs, Chicago, Illinois), as desired. The compounds according to the method of the invention and the anti-coagulant agent, anti-platelet agent, thrombin inhibitor, thrombolytic agent, and/or combinations thereof, may be separate, or combined into a single dosage form as described above. Such kits may further include, if desired, one or more of various conventional pharmaceutical kit components, such as for example, one or more pharmaceutically acceptable carriers, additional vials for mixing the components, etc., as will be readily apparent to those skilled in the art. Instructions, either as inserts or as labels, indicating quantities of the components to be administered, guidelines for administration, and/or guidelines for mixing the components, may also be included in the kit.

__________________________________________________________________________

##STR59##

Ex.

No. R.sup.1 R.sup.10

R.sup.13

R.sup.14

R.sup.15 MS

__________________________________________________________________________

1001

imidazol-2-ylamino-(CH.sub.2).sub.3

›H H H H

1002

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 Ph

1003

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(2-CH.sub.3)

1004

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(3-CH.sub.3)

1005

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(4-CH.sub.3)

1006

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-pyridinyl)

1007

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (3-pyridinyl)

1008

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-pyridinyl)

1009

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

1010

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-thiazolyl)

1011

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (5-thiazolyl)

1012

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-isoxazolyl)

1013

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thienyl)

1014

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (5-isoxazolyl)

1015

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 n-Bu

1016

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

1017

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 t-Bu

1017a

imidazol-2-ylamino-(CH.sub.2).sub.3

›H H H NHCOPh

1018

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 Ph

1019

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

1020

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

1021

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

1021a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 CH.sub.2 Ph

1021b

imidazol-2-ylamino-(CH.sub.2).sub.3

›H H H NHCOCHCHPh

1022

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (2-pyridinyl)

1023

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (3-pyridinyl)

1024

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (4-pyridinyl)

1025

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (2-thiazolyl)

1026

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (4-thiazolyl)

1027

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (5-thiazolyl)

1028

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (4-isoxazol)

1029

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (2-thienyl)

1029a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (cyclohexyl)

1029b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO-cyclohexyl

1030

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOn-Bu

1031

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOt-Bu

1031a

imidazol-2-ylamino-(CH.sub.2).sub.3

›H H H NHCONHPh · 1 of 7

1031b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCONHCH.sub.2 Ph

1032

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph 512.3

1033

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

1034

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

1035

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

1035a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-CH.sub.3).sub.2

540.4

1035b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

554.4

1036

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-pyridyl)

1037

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-pyridyl)

1038

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-pyridyl)

1038a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thienyl)

1038b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 3-(2,5-

dichloro)thienyl!

1039

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiaz-olyl)

1040

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-thiazolyl)

1040a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 5-(4-methyl-2-

amino)thiazolyl!

1041

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

1042

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

1043

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-Br)

1044

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

1045

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Br)

1046

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(2-F)

1047

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

1048

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-F)

1048a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

580.2

1049

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

1050

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

562.4

1050a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph) 588.4

1050b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-

pyridyl)

1050c

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-

oxazolyl)

1050d

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-

pyrazolyl)

1050e

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-Ph-2,6- 616.3

dimethyl

1050f

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)-2,6-dimethyl

1050g

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxa-

zolyl)-2,6-dimethyl

1050h

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyra-

zolyl)-2,6-dimethyl

1050i

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-Ph-2,6-

dichloro

1050j

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-furyl) 578.3

1050k

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)

1050l

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)

1050m

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(4-

pyridyl)-2,6-dimethyl

1050n

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)-

2,6-dimethyl

1050o

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-furyl)-

2,6-dichloro

1051

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CHCHPh

1052

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

1053

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 CHCHPh

1054

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -n-Bu

1055

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -i-Bu

1056

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -t-Bu

1057

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

1058

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(2-CH.sub.3)

1059

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(3-CH.sub.3)

1060

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

1060a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

1060b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

1061

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-pyridyl)

1062

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(3-pyridyl)

1063

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(4-pyridyl)

1064

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-thiazolyl)

1065

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(4-thiazolyl)

1066

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(4-isoxazolyl)

1067

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

1068

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(2-Br)

1069

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(3-Br)

1070

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Br)

1071

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(3-F)

1072

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-F)

1073

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

1074

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(1-naphthyl)

1074a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

1074b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

1074c

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

1075

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCHCHPh

1076

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 Ph

1077

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 CHCHPh

1077a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH-cyclohexyl

1078

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH-n-Bu

1079

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH-i-Bu

1080

›H H H NHCONHPh · 2 of 7

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH-t-Bu

1081

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 Ph

517.3

1082

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(2-CH.sub.3)

1083

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(3-CH.sub.3)

1084

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(4-CH.sub.3)

1085

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-pyridinyl)

1086

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (3-pyridinyl)

1087

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-pyridinyl)

1088

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

1089

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-thiazolyl)

1090

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (5-thiazolyl)

1091

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-isoxazolyl)

1092

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thienyl)

1093

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 n-Bu

1094

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

483.5

1095

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 t-Bu

1095a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOPh 487.3

1096

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 Ph

501.4

1097

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

1098

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

1099

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

1099a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 CH.sub.2 Ph

515.4

1099b

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCHCHPh 513.3

1100

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (2-pyridinyl)

1101

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (3-pyridinyl)

1102

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (4-pyridinyl)

1103

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (2-thiazolyl)

1104

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (4-thiazolyl)

1105

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (5-thiazolyl)

1106

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 CH.sub.2 CH(CH.sub.3)

.sub.2 481.4

1107

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (4-isoxazolyl)

1108

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (2-thienyl)

1108a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (cyclohexyl)

507.3

1108b

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO-cyclohexyl

493.4

1109

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOn-Bu

1110

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOt-Bu

1110a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCONHPh 502.4

1110b

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCONHCH.sub.2 Ph

516.5

1111

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph 523.2

1112

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

1113

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

1114

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

1114a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-CH.sub.3).sub.2

1114b

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

565.2

1115

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-pyridyl)

1116

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-pyridyl)

1117

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-pyridyl)

1117a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thienyl)

529.2

1117b

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 3-(2,5-

597.1

dichloro)thienyl!

1118

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

1119

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-thiazolyl)

1119a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 5-(4-methyl-2-

559.2

amino)thiazolyl!

1120

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

1121

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

542.2

dimethyl)isoxazolyl!

1122

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-Br)

1123

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

1124

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Br)

1125

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(2-F)

1126

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

1127

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-F)

1127a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

591.3

1128

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

573.4

1129

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

573.2

1129a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph) 599.4

1129b

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-

pyridyl)

1129c

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-

oxazolyl)

1129d

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-

pyrazolyl)

1129e

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-Ph-2,6-

dimethyl

1129f

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)-2,6-dimethyl

1129g

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxa-

zolyl)-2,6-dimethyl

1129h

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyra-

zolyl)-2,6-dimethyl

1129i

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-Ph-2,6-

dichloro

1129j

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-furyl)

1129k

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)

1129l

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)

1129m

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(4-

pyridyl)-2,6-dimethyl

1129n

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)-

2,6-dimethyl

1129o

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

›H H H NHCONHPh · 3 of 7

-4-(2-furyl)-

2,6-dichloro

1130

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CHCHPh

1131

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

537.4

1132

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 CHCHPh

1133

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -n-Bu

503.3

1134

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -i-Bu

1135

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -t-Bu

1136

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

1137

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(2-CH.sub.3)

1138

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(3-CH.sub.3)

1139

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

1139a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

1139b

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6- 580.3

Me.sub.3)

1140

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-pyridyl)

1141

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(3-pyridyl)

1142

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(4-pyridyl)

1143

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-thiazolyl)

1144

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH-(4-thiazolyl)

1145

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(4-isoxazolyl)

1146

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

1147

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(2-Br)

1148

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(3-Br)

1149

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Br)

1150

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(3-F)

1151

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-F)

1152

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

1153

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH)1-naphthyl)

1153a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

1153b

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

1153c

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

1154

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCHCHPh

1155

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 Ph

552.4

1156

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 CHCHPh

1156a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSONH-cyclohexyl

544.4

1157

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH-n-Bu

1158

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH-i-Bu

518.4

1159

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH-t-Bu

1160

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOOCH.sub.2 Ph

1161

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(2-CH.sub.3)

1162

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(3-CH.sub.3)

1163

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(4-CH.sub.3)

1164

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-pyridinyl)

1165

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (3-pyridinyl)

1166

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-pyridinyl)

1167

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

1168

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-thiazolyl)

1169

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H, H NHCO.sub.2 CH.sub.2 (5-thiazolyl)

1170

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-isoxazolyl)

1171

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thienyl)

1172

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 n-Bu

1173

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

1174

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 t-Bu

1175

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

1176

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

1177

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

1178

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

1178a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

1178b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

570.5

1179

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-pyridyl)

1180

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-pyridyl)

1181

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-pyridyl)

1181a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thienyl)

1181b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 3-(2,5-

dichloro)thienyl!

1182

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

1183

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-thiazolyl)

1184

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

1185

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

1186

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-Br)

1187

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

1188

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(2-F)

1189

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

1190

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-F)

1190a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

1191

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

1192

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

1192a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H H H NHCONHPh · 4 of 7

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

1192b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-

pyridyl)

1192c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-

oxazolyl)

1192d

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-

pyrazolyl)

1192e

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-Ph-2,6-

dimethyl

1192f

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)-2,6-dimethyl

1192g

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxa-

zolyl)-2,6-dimethyl

1192h

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyra-

zolyl)-2,6-dimethyl

1192i

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-Ph-2,6-

dichloro

1192j

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-furyl)

1192k

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)

1192l

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)

1192m

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(4-

pyridyl)-2,6-dimethyl

1192n

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)-

2,6-dimethyl

1192o

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-furyl)-

2,6-dichloro

1193

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CHCHPh

1194

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

1195

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 CHCHPh

1196

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -n-Bu

1197

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -i-Bu

1197a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

1197b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(2-CH.sub.3)

1197c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(3-CH.sub.3)

1197d

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

1197e

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

1197f

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

1197g

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

1197h

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

1197j

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(1-naphthyl)

1197k

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

1197m

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

1197n

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

1197p

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 Ph

1198

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOOCH.sub.2 Ph

508.6

1199

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(2-CH.sub.3)

1200

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(3-CH.sub.3)

1201

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(4-CH.sub.3)

1202

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-pyridinyl)

1203

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (3-pyridinyl)

1204

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-pyridinyl)

1205

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

1206

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-thiazolyl)

1207

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (5-thiazolyl)

1208

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-isoxazolyl)

1209

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thienyl)

1210

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 n-Bu

1211

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

1212

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 t-Bu

1213

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph 514.3

1214

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

1215

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

1216

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

1216a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

1216b

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

556.4

1217

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-pyridyl)

1218

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-pyridyl)

1219

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-pyridyl)

1219a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thienyl)

1219b

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 3-(2,5-

dichloro)thienyl!

1220

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

1220a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 5-(4-methyl-2-

amino)thiazolyl!

1221

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

1222

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

1223

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-Br)

1224

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

1225

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(2-F)

1226

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

1227

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-F)

1227a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

1228

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

›H H H NHCONHPh · 5 of 7

1229

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

1229a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

1229b

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-

pyridyl)

1229c

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-

oxazolyl)

1229d

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-

pyrazolyl)

1229e

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-Ph-2,6-

dimethyl

1229f

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)-2,6-dimethyl

1229g

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxa-

zolyl)-2,6-dimethyl

1229h

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyra-

zolyl)-2,6-dimethyl

1229i

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-Ph-2,6-

dichloro

1229j

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-furyl)

1229k

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)

1229l

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)

1229m

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(4-

pyridyl)-2,6-dimethyl

1229n

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)-

2,6-dimethyl

1229o

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-furyl)-

2,6-dichloro

1230

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CHCHPh

1231

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

1232

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 CHCHPh

1233

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -n-Bu

1234

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -i-Bu

1234a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

1234b

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(2-CH.sub.3)

1234c

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(3-CH.sub.3)

1234d

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

1234e

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

1234f

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

1234g

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

1234h

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH)1-naphthyl)

1234j

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

1234m

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

1234n

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

1234p

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 Ph

1235

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

1236

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

1237

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

1238

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

1238a

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

1238b

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

1239

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-pyridyl)

1240

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-pyridyl)

1241

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-pyridyl)

1241a

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thienyl)

1241b

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 3-(2,5-

dichloro)thienyl!

1242

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

1242a

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 5-(4-methyl-2-

amino)thiazolyl!

1243

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

1244

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

1245

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-Br)

1246

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

1247

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(2-F)

1248

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

1249

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-F)

1249a

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

1249b

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

1249c

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

1249d

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

1249e

benzimidazol-2-ylamino(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

1249f

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

1249g

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CHCHPh

1249h

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

1249j

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 CHCHPh

1249k

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -n-Bu

1249m

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -i-Bu

1249n

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

1249p

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(2-CH.sub.3)

1249q

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(3-CH.sub.3)

1249r

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

1249s

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

1249t

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

1249u

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

1249v

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH)1-naphthyl)

1249w

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H H H NHCONHPh · 6 of 7

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

1249x

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

1249y

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

1249z

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 Ph

1250

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 Ph

1251

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 n-Bu

1252

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

1253

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

1254

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

1255

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

1256

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

1256a

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

1256b

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

1257

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-pyridyl)

1258

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H W NHSO.sub.2 (3-pyridyl)

1259

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-pyridyl)

1260

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

1261

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

1262

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

1263

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-Br)

1264

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

1265

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(2-F)

1266

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

1267

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-F)

1267a

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

1267b

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

1267c

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

1267d

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

1267e

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

1267f

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

1267g

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 CHCHPh

1267h

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

1267j

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 CHCHPh

1267k

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 -n-Bu

1267m

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 -i-Bu

1267n

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

1267p

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(2-CH.sub.3)

1267q

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(3-CH.sub.3)

1267r

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

1267s

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

1267t

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

1267u

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

1267v

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH)1-naphthyl)

1267w

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

1267x

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

1267y

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

1268

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 Ph

1269

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHCO.sub.2 n-Bu

1270

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

1271

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

1274

imidazol-4-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

1279

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

1282

imidazol-4-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

1287

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

1290

imidazol-4-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

1295

imidazol-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

1296

pyridin-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

1297

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

1298

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

1299

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

1300

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H 3-pyridinyl

1301

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H 3-pyridinyl

1304

imidazol-4-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

1309

imidazol-2-ylamino-(CH.sub.2).sub.3

H H (3,4-methylene-

dioxy)phenyl

1310

pyridin-2-ylamino-(CH.sub.2).sub.3

H H (3,4-methylene-

dioxy)phenyl

1311

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H (3,4-methylene-

dioxy)phenyl

1312

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H (3,4-methylene-

dioxy)phenyl

1313

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H (3,4-methylene-

dioxy)phenyl

1314

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H (3,4-methylene-

dioxy)phenyl

1315

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H (3,4-methylene-

dioxy)phenyl

1318

imidazol-4-ylamino-(CH.sub.2).sub.3

H H (3,4-methylene-

dioxy)phenyl

1323

imidazol-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

NHSO.sub.2 Ph

1324

pyridin-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

NHSO.sub.2 Ph

1325

imidazol-2-ylamino-(CH.sub.2).sub.3

H H (3,4-methylene-

NHSO.sub.2 Ph

dioxy)phenyl

1326

pyridin-2-ylamino-(CH.sub.2).sub.3

H H (3,4-methylene-

NHSO.sub.2 Ph

dioxy)phenyl

1326a

pyridinyl-2-ylamino(CH.sub.2).sub.2 CH(Ph)

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

641.4

1326b

pyridin-2-ylamino-(CH.sub.2).sub.2 CH(CH.sub.3)

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

579.4

1326c

pyridin-2-ylamino-CH.sub.2 CH(CH.sub.3)CH.sub.2

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

579.5

1326d

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

1326e

pyridin-2-ylamino-(CH.sub.2).sub.3

›H H H NHCONHPh · 7 of 7

C.sub.2 H.sub.5

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

1326f

pyridin-2-ylamino-(CH.sub.2).sub.3

Ph H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

641.4

1326g

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 Ph

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

669.5

1326h

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

579.4

1326i

imidazol-2-ylamino-(CH.sub.2).sub.2

H H Me NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

568.3

1327

imidazol-2-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

1327a

imidazol-2-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1327b

imidazol-2-ylamino-carbonyl-(CH.sub.2).sub.2

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

568.5

1328

pyridin-2-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

1328a

pyridin-2-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1328b

pyridin-2-ylamino-carbonyl-(CH.sub.2).sub.2

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

1329

imidazolin-2-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

1329a

imidazolin-2-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

494.3

1330

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

1330a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1331

benzimidazol-2-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

1331a

benzimidazol-2-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1331b

benzimidazol-2-ylamino-carbonyl-

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

(CH.sub.2).sub.2

1332

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

1332a

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1333

2-iminoazepin-7-yl-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

1333a

2-iminoazepin-7-yl-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1336

imidazol-4-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

1336a

imidazol-4-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1341

imidazol-2-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

1341a

imidazol-2-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

1342

pyridin-2-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

1342a

pyridin-2-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

1343

imidazolin-2-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

1343a

imidazolin-2-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

522.3

1344

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

1344a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

1345

benzimidazol-2-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

1345a

benzimidazol-2-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

1346

2-aminopyridin-6-yl-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

1346a

2-aminopyridin-6-yl-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

1347

2-iminoazepin-7-yl-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

1347a

2-iminoazepin-7-yl-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

1350

imidazol-4-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

1350a

imidazol-4-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

1351

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 -(1-naphthyl)

1352

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1353

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

1354

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 -(1-naphthyl)

1355

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1356

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

1357

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 -(1-naphthyl)

1358

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1359

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

1360

imidazolin-2-ylamino-(o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 -(1-naphthyl)

1361

imidazolin-2-ylamino-(o-C.sub.6 H.sub.4)CH.sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

1362

imidazolin-2-ylamino-(o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

__________________________________________________________________________

##STR60##

Ex.

No. R.sup.1a R.sup.10

R.sup.13

R.sup.14

R.sup.15 MS

__________________________________________________________________________

2001

imidazol-2-ylamino-(CH.sub.2).sub.3

›H H H H

2002

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOOCH.sub.2 Ph

2003

imidazolin-2-yl amino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

2004

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

2005

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

2006

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-pyridinyl)

2007

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (3-pyridinyl)

2010

imidazol-4-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

2015

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-isoxazolyl)

2016

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thienyl)

2017

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 n-Bu

2018

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

2019

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 t-Bu

2020

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

2021

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub

.3)

2024

imidazol-4-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-pyridyl)

2029

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

2030

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-dim-

ethyl)isoxazolyl!

2031

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(2-Br)

2032

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-Br)

2033

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-Br)

2034

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(2-F)

2035

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

2038

imidazol-4-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

2043

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -i-Bu

2044

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -t-Bu

2045

imidazol-2-ylamino-(CH.sub.2).sub.3

H H (3,4- H

methylenedioxy)

phenyl

2046

pyridin-2-ylamino-(CH.sub.2).sub.3

H H (3,4- H

methylenedioxy)

phenyl

2047

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H (3,4- H

methylenedioxy)

phenyl

2048

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H (3,4- H

methylenedioxy)

phenyl

2049

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H (3,4- H

methylenedioxy)

phenyl

2050

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H (3,4- H

methylenedioxy)

phenyl

2051

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H (3,4-

methylenedioxy)

phenyl

2054

imidazol-4-ylamino-(CH.sub.2).sub.3

H H (3,4- H

methylenedioxy)

phenyl

2059

imidazol-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

2060

pyridin-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

2061

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

2062

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

2063

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

2064

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H 3-pyridinyl

2065

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H 3-pyridinyl

2068

imidazol-4-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

2073

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOOCH.sub.2 Ph

508.3

2075

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 Ph

2076

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

2077

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (3 -pyridinyl)

2078

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

2079

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thienyl)

2080

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (5-isoxazolyl)

2081

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 n-Bu

2082

imidazol-2-ylamino-(CH.sub.2).sub.3

›H H H NHCOPh

2083

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 Ph

2084

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 CH.sub.2 Ph

2085

imidazol-2-ylamino-(CH.sub.2).sub.3

›H H H NHCOCHCHPh

2086

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (3-pyridinyl)

2087

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (2-thienyl)

2088

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (cyclohexyl)

2089

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCOn-Bu

2090

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCONHCH.sub.2 Ph

2091

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

2092

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub

.3)

2093

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.s

ub.3).sub.2 540.3

2094

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH

.sub.3).sub.3

554.4

2095

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-pyridyl)

2096

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thienyl)

2097

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

2098

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

2099

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-Br)

2100

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-F)

2101

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.s

ub.2)

2102

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

2103

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

562.4

2104

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-Ph

588.4

2104a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-

pyridyl)

2104b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-

oxazolyl)

2104c

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-

pyrazolyl)

2105

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

616.3

dimethyl

2105a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)-2,6-dimethyl

2105b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(2-oxa-

zolyl)-2,6-dimethyl

2105c

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-pyra

zolyl)-2,6-dimethyl

2106

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dichloro

2107

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H-4-Ph-2,6-

dimethyl-3-chloro

2108

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

2109

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -n-Bu

2110

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

2111

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

2112

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

2113

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

2114

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(3-pyridyl)

2115

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

2116

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Br)

2117

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-F)

2118

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

2119

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(1-naphthyl)

2120

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

2121

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

2122

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

2123

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 Ph

2124

imidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH-n-Bu

2125

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

2126

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (3-pyridinyl)

2127

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

2128

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (4-isoxazolyl)

2129

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

2130

pyridin-2-ylamino-(CH.sub.2).sub.3

›H H H NHCOPh

2131

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 Ph

2132

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 CH.sub.2 Ph

2133

pyridin-2-ylamino-(CH.sub.2).sub.3

›H H H NHCOCHCHPh · 1 of 4

2134

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (3-pyridinyl)

2135

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (2-thienyl)

2136

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOCH.sub.2 (cyclohexyl)

2137

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOn-Bu

2138

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHCONHCH.sub.2 Ph

2139

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

2140

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub

.3)

2141

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.s

ub.3).sub.2

2142

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH

.sub.3).sub.3

565.4

2143

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-pyridyl)

2144

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thienyl)

2145

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

2146

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-Br)

2147

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-F)

2148

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.s

ub.2)

2149

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

2150

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

2151

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

2151a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-

pyridyl)

2151b

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-

oxazolyl)

2151c

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-

pyrazolyl)

2152

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dimethyl

2152a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)-2,6-dimethyl

2152b

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(2-oxa-

zolyl)-2,6-dimethyl

2152c

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-pyra

zolyl)-2,6-dimethyl

2153

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dichloro

2154

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

2155

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -n-Bu

2156

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

2157

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

2158

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

2159

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

2160

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(3-pyridyl)

2161

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

2162

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Br)

2163

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-F)

2164

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

2165

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH)1-naphthyl)

2166

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

2167

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

2168

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

2169

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 Ph

2170

pyridin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH-n-Bu

2171

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCOOCH.sub.2 Ph

2172

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

2173

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (3-pyridinyl)

2173

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

2175

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thienyl)

2176

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 n-Bu

2177

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

2178

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub

.3)

2179

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Me.s

ub.2)

2180

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-Me

.sub.3)

2181

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-pyridyl)

2182

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thienyl)

2183

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

2184

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(2-Br)

2185

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-F)

2186

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.s

ub.2)

2187

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

2188

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

2189

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

2189a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-

pyridyl)

2189b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-

oxazolyl)

2189c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-

pyrazolyl)

2190

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dimethyl

2190a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)-2,6-dimethyl

2190b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(2-oxa-

zolyl)-2,6-dimethyl

2190c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-pyra

zolyl)-2,6-dimethyl

2191

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dichloro

2192

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

2193

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -n-Bu

2194

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H H H NHCOCHCHPh · 2 of 4

H H H NHSO.sub.2 NHPh

2195

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

2196

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

2197

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

2198

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

2199

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

2200

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(1-naphthyl)

2201

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

2202

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dimethyl)

2203

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-

dichloro)

2204

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 Ph

2205

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

2206

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (3-pyridinyl)

2207

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

2208

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 (2-thienyl)

2209

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

2210

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

2211

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub

.3)

2212

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Me.s

ub.2)

2213

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-Me

.sub.3)

2214

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-pyridyl)

2215

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thienyl)

2216

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

2217

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

2218

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-Br)

2218

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-F)

2219

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.s

ub.2)

2220

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

2221

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

2222

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

2222a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-

pyridyl)

2222b

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-

oxazolyl)

2222c

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-

pyrazolyl)

2223

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dimethyl

2223a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-

pyridyl)-2,6-dimethyl

2223b

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(2-oxa-

zolyl)-2,6-dimethyl

2223c

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-(3-pyra

zolyl)-2,6-dimethyl

2224

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dichloro

2225

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

2226

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -n-Bu

2227

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

2228

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

2229

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

2230

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

2231

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

2232

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH)1-naphthyl)

2233

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

2234

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-4-Ph-2,6-

dimethyl

2235

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-4-Ph-2,6-

dichloro

2236

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 Ph

2237

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

2238

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub

.3)

2239

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Me.s

ub.2)

2240

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-Me

.sub.3)

2241

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-pyridyl)

2242

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thienyl)

2243

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

2244

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

2245

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-Br)

2246

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

2247

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.s

ub.2)

2248

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

2249

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

2250

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

2251

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dimethyl

2252

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dichloro

2253

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

2254

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 -i-Bu

2255

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

2256

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

2257

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

2258

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

2259

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

›H H H NHCOCHCHPh · 3 of 4

2260

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH)1-naphthyl)

2261

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

2262

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-4-Ph-2,6-

dimethyl

2263

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-4-Ph-2,6-

dichloro

2264

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHCH.sub.2 Ph

2265

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 CH.sub.2 Ph

2266

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

2267

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub

.3)

2268

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Me.s

ub.2)

2269

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-Me

.sub.3)

2270

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (3-pyridyl)

2271

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-thiazolyl)

2272

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

2273

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-Br)

2274

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

2275

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.s

ub.2)

2276

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (2-naphthyl)

2277

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (1-naphthyl)

2278

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

2279

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dimethyl

2280

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 C.sub.6 H.sub.2 -4-Ph-2,6-

dichloro

2281

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 CH.sub.2 Ph

2282

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 -i-Bu

2283

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHPh

2284

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

2285

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

2286

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-

Me.sub.3)

2287

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH(2-naphthyl)

2288

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NH)1-naphthyl)

2289

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

2290

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-4-Ph-2,6-

dimethyl

2291

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 NHC.sub.6 H.sub.2

-4-Ph-2,6-

dichloro

2292

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHCO.sub.2 n-Bu

2293

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H H NHCO.sub.2 i-Bu

2294

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

2295

imidazol-4-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 Ph

2296

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

2297

imidazol-4-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 (4-isoxazolyl)

2298

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

2299

imidazol-4-ylamino-(CH.sub.2).sub.3

H H H NHSO.sub.2 - 4-(3,5-

dimethyl)isoxazolyl!

2300

imidazol-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

NHSO.sub.2 Ph

2301

pyridin-2-ylamino-(CH.sub.2).sub.3

H H 3-pyridinyl

NHSO.sub.2 Ph

2302

imidazol-2-ylamino-(CH.sub.2).sub.3

H H (3,4-methylene-

NHSO.sub.2 Ph

dioxy)phenyl

2303

pyridin-2-ylamino-(CH.sub.2).sub.3

H H (3,4-methylene-

NHSO.sub.2 Ph

dioxy)phenyl

2304

imidazol-2-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

2305

imidazol-2-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2306

imidazol-2-ylamino-carbonyl-(CH.sub.2).sub.2

H H H NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH

.sub.3).sub.3

2307

pyridin-2-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

2308

pyridin-2-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2309

pyridin-2-ylamino-carbonyl-(CH.sub.2).sub.2

H H H NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH

.sub.3).sub.3

2310

imidazolin-2-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

2311

imidazolin-2-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2312

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

2313

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2314

benzimidazol-2-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

2315

benzimidazol-2-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2316

benzimidazol-2-ylamino-carbonyl-(CH.sub.2).sub.2

H H H NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH

.sub.3).sub.3

2317

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

2318

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2319

2-iminoazepin-7-yl-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

2320

2-iminoazepin-7-yl-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2321

imidazol-4-ylamino-(CH.sub.2).sub.2

H H H NHSO.sub.2 Ph

2322

imidazol-4-ylamino-(CH.sub.2).sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2323

imidazol-2-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

2324

imidazol-2-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

2325

pyridin-2-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

2326

pyridin-2-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

2327

imidazolin-2-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

2328

imidazolin-2-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

522.3

2329

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

2330

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

2331

benzimidazol-2-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

2332

benzimidazol-2-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

2333

2-aminopyridin-6-yl-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

2334

2-aminopyridin-6-yl-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

2335

2-iminoazepin-7-yl-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

2336

2-iminoazepin-7-yl-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

2337

imidazol-4-ylamino-(CH.sub.2).sub.4

H H H NHSO.sub.2 Ph

2338

imidazol-4-ylamino-(CH.sub.2).sub.4

H H H NHCO.sub.2 CH.sub.2 Ph

2339

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 -(1-naphthyl)

2340

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2341

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

›H H H NHCOCHCHPh · 4 of 4

H H H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me

.sub.3)

2342

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 -(1-naphthyl)

2343

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2344

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me

.sub.3)

2345

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 -(1-naphthyl)

2346

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2347

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me

.sub.3)

2348

imidazolin-2-ylamino-(o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 -(1-naphthyl)

2349

imidazolin-2-ylamino-(o-C.sub.6 H.sub.4)CH.sub.2

H H H NHCO.sub.2 CH.sub.2 Ph

2350

imidazolin-2-ylamino-(o-C.sub.6 H.sub.4)CH.sub.2

H H H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me

.sub.3)

__________________________________________________________________________

##STR61##

Ex. No.

R.sup.1 R.sup.9

R.sup.14 R.sup.15 MS

__________________________________________________________________________

3001

imidazol-2-ylamino-(CH.sub.2).sub.3

›H H H · 1 of 2

3002

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHCOOCH.sub.2 Ph

3002a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHCOOCH.sub.2 Ph

3002b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 Ph

3002c

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 Ph

3003

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(2-CH.sub.3)

3004

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(3-CH.sub.3)

3005

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(4-CH.sub.3)

3006

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 (2-pyridinyl

)

3007

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 (3-pyridinyl

)

3010

imidazol-4-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 (2-thiazolyl

)

3015

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 (4-isoxazoly

3016

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 (2-thienyl)

3017

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 n-Bu

3018

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 i-Bu

3019

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 t-Bu

3020

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H NHSO.sub.2 Ph

3020a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 Ph

3020b

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 Ph

3020c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 Ph

3020d

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 Ph

3021

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

3021a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

3021b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

3021c

imidazo1-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-Ph)

3021d

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-Ph)

3021e

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-Ph)

3021f

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-Ph)

3021g

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(3-pyridyl)

3021h

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(4-pyridyl)

3021i

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(2-furyl)

3021j

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(3-furyl)

3021k

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(5-pyrazolyl))

3021l

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

3021m

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(3-pyridyl))

3021n

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(4-pyridyl))

3021o

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

(2,6-Me.sub.2 -4-(2-furyl))

3021p

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(3-furyl))

3021q

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(5-pyrazolyl))

3021r

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

3021s

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(3-pyridyl))

3021t

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2 -

(2,6-Me.sub.2 -4-(4-pyridyl))

3021u

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(2-furyl))

3021v

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(3-furyl))

3021w

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-(5-pyrazolyl))

3024

imidazol-4-ylamino-(CH.sub.2).sub.3

H H. NHSO.sub.2 (2-pyridyl)

3029

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 (4-isoxazolyl)

3030

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

3030a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

3030b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 - 4-(3,5

dimethyl)isoxazolyl!

3030c

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

3031

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-Br)

3032

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

3033

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Br)

3034

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-F)

3035

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-F)

3038

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 (1-naphthyl)

3038a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

3038b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Cl.sub.2 -4-Ph)

3043

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 -i-Bu

3044

pyridin-2-ylamino-(CH.sub.2)3

H H NHSO.sub.2 -t-Bu

3045

imidazol-2-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

3046

pyridin-2-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

3047

imidazolin-2-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

3048

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

3049

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

3050

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

3051

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

3054

imidazol-4-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

3059

imidazol-2-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

3060

pyridin-2-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

3061

imidazolin-2-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

3062

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

3063

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

3064

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H 3-pyridinyl H

3065

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H 3-pyridinyl H

3068

imidazol-4-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

3068a

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

›H H H · 2 of 2

H H NHSO.sub.2 -(1-naphthyl)

3068b

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHCO.sub.2 CH.sub.2 Ph

3068c

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3068d

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 -(1-naphthyl)

3068e

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHCO.sub.2 CH.sub.2 Ph

3068f

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3068g

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 -(1-naphthyl)

3068h

imidazolin-2-ylamino-CH.sub.2 (6-C.sub.6 H.sub.4)

H H NHCO.sub.2 CH.sub.2 Ph

3068i

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3068j

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H H NHSO.sub.2 -(1-naphthyl)

3068k

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H H NHCO.sub.2 CH.sub.2 Ph

3068l

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3075

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3076

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(3-CH.sub.3)

3077

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (3-pyridinyl

)

3078

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thiazolyl

)

3079

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thienyl)

3080

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (5-isoxazoly

3081

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 n-Bu

3082

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›H NHCOPh

3083

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 Ph *

3084

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 CH.sub.2 Ph

3085

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›H NHCOCH═CHPh

3086

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (3-pyridinyl)

3087

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (2-thienyl)

3088

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (cyclohexyl)

3089

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOn-Bu

3090

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCONHCH.sub.2 Ph

3091

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

3092

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

3093

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-CH.sub.3).sub.2

554.4

3094

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

568.4

3095

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (3-pyridyl)

3096

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thienyl)

3097

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

3098

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 4-(3,5-dimethyl)isox

azolyl!

3099

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Br)

3100

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-F)

3101

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2) 594.3

3102

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

3103

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

3104

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

3104a

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(4-pyridyl)

3104b

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-oxazolyl)

3104c

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(3-pyrazolyl)

3105

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

630.3

3105a

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyridyl)-2,6-dimethyl

3105b

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxazolyl)-2,6-dimethyl

3105c

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyrazolyl)-2,6-dimethyl

3105d

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(4-pyridyl)-2,6-dimethyl

3105e

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-furyl)-2,6-dimethyl

3105f

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)-2,6-dimethyl

3106

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

670.3

3107

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H-(4-Ph-2,6-d

imethyl-3-chloro)

3108

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

3109

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -n-Bu

3110

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

3111

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

3112

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

3113

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3114

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(3-pyridyl)

3115

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 4-(3,5-dimethyl)isox

azolyl!

3116

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Br)

3117

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-F)

3118

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

3119

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(1-naphthyl)

3120

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

3121

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3122

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3123

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHCH.sub.2 Ph

3124

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH-n-Bu

3125

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(3-CH.sub.3)

3126

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (3-pyridinyl

)

3127

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thiazolyl

)

3128

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (4-isoxazoly

3129

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 i-Bu

3130

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›H NHCOPh

3131

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 Ph

3132

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 CH.sub.2 Ph

3133

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›H NHCOCH═CHPh · 1 of 4

3134

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (3-pyridinyl)

3135

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (2-thienyl)

3136

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (cyclohexyl)

3137

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOn-Bu

3138

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCONHCH.sub.2 Ph

3139

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

3140

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

3141

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-CH.sub.3).sub.2

3142

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

579.4

3143

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (3-pyridyl)

3144

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thienyl)

3145

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

3146

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Br)

3147

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-F)

3148

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

3149

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

3150

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

3151

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

3151a

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(4-pyridyl)

3151b

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-oxazolyl)

3151c

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(3-pyrazolyl)

3152

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3152a

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyridyl)-2,6-dimethyl

3152b

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxazolyl)-2,6-dimethyl

3152c

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyrazolyl)-2,6-dimethyl

3152d

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(4-pyridyl)-2,6-dimethyl

3152e

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-furyl)-2,6-dimethyl

3152f

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)-2,6-dimethyl

3153

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3154

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

3155

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -n-Bu

3156

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

3157

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

3158

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

3159

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3160

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(3-pyridyl)

3161

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

3162

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Br)

3163

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-F)

3164

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

3165

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH)1-naphthyl)

3166

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

3167

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3168

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3169

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHCH.sub.2 Ph

3170

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH-n-Bu

3171

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOOCH.sub.2 Ph

3172

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(4-CH.sub.3)

3173

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (3-pyridinyl

)

3173

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thiazolyl

)

3175

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thienyl)

3176

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 n-Bu

3177

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

3178

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

3179

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

3180

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

3181

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (3-pyridyl)

3182

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thienyl)

3183

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

3184

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(2-Br)

3185

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-F)

3186

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

3187

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

3188

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

3189

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

3189a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(4-pyridyl)

3189b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-oxazolyl)

3189c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(3-pyrazolyl)

3190

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3190a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyridyl)-2,6-dimethyl

›H NHCOCH═CHPh · 2 of 4

3190b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxazolyl)-2,6-dimethyl

3190c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyrazolyl)-2,6-dimethyl

3190d

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(4-pyridyl)-2,6-dimethyl

3190e

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-furyl)-2,6-dimethyl

3190f

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)-2,6-dimethyl

3191

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3192

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

3193

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -n-Bu

3194

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

3195

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

3196

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

3197

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3198

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 4-(3,5-dimethyl)isox

azolyl!

3199

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

3200

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(1-naphthyl)

3201

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

3202

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3203

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3204

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHCH.sub.2 Ph

3205

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(4-CH.sub.3)

3206

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (3-pyridinyl

)

3207

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thiazolyl

)

3208

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thienyl)

3209

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 i-Bu

3210

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

3211

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

3212

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

3213

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

3214

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (3-pyridyl)

3215

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thienyl)

3216

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

3217

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

3218

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

3218a

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-F)

3219

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

3220

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

3221

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

3222

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

3222a

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(4-pyridyl)

3222b

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-oxazolyl)

3222c

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(3-pyrazolyl)

3223

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3223a

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyridyl)-2,6-dimethyl

3223b

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxazolyl)-2,6-dimethyl

3223c

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyrazolyl)-2,6-dimethyl

3223d

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(4-pyridyl)-2,6-dimethyl

3223e

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-furyl)-2,6-dimethyl

3223f

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-furyl)-2,6-dimethyl

3224

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3225

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

3226

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -n-Bu

3227

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

3228

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

3229

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

3230

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3231

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

3232

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH)1-naphthyl)

3233

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

3234

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3235

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3236

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHCH.sub.2 Ph

3237

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

3238

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

3239

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

3240

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

3241

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (4-pyridyl)

3242

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H NHCOCH═CHPh · 3 of 4

CH.sub.3

H NHSO.sub.2 (2-thienyl)

3243

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

3244

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

3245

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

3246

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-F)

3247

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

3248

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

3249

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

3250

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

3251

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3252

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3253

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

3254

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -i-Bu

3255

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

3256

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

3257

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

3258

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3259

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

3260

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH)1-naphthyl)

3261

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

3262

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3263

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3264

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHCH.sub.2 Ph

3265

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3266

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 i-Bu

3267

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

3268

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

3269

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

3270

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (3-pyridyl)

3271

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

3272

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (4-isoxazolyl)

3273

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

3274

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-F)

3275

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

3276

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

3277

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

3278

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

3279

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3280

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3281

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

3282

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -i-Bu

3283

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

3284

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

3285

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

3286

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3287

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

3288

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH)1-naphthyl)

3289

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

3290

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

3291

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

3292

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 n-Bu

3293

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 i-Bu

3294

2-iminoazepin-7-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

3295

imidazol-4-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

3296

2-iminoazepin-7-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (4-isoxazolyl)

3297

imidazol-4-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (4-isoxazolyl)

3298

2-iminoazepin-7-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

3299

imidazol-4-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

3300

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

3-pyridinyl NHSO.sub.2 Ph

3301

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

3-pyridinyl NHSO.sub.2 Ph

3302

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

(3,4-methylenedioxy)phenyl

NHSO.sub.2 Ph

3303

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

(3,4-methylenedioxy)phenyl

NHSO.sub.2 Ph

3304

imidazol-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

3305

imidazol-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3306

imidazol-2-ylamino-carbonyl-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3307

pyridin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

3308

pyridin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3309

pyridin-2-ylamino-carbonyl-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3310

imidazolin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

3311

imidazolin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3312

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

3313

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3314

benzimidazol-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

3315

benzimidazol-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3316

benzimidazol-2-ylamino-carbonyl-(CH.sub.2).sub.2

›H NHCOCH═CHPh · 4 of 4

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3317

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

3318

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3319

2-iminoazepin-7-yl-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

3320

2-iminoazepin-7-yl-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3321

imidazol-4-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

3322

imidazol-4-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3323

imidazol-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

3324

imidazol-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3325

pyridin-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

3326

pyridin-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3327

imidazolin-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

3328

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

3329

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3330

benzimidazol-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

3331

benzimidazol-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3332

2-aminopyridin-6-yl-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

3333

2-aminopyridin-6-yl-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3334

2-iminoazepin-7-yl-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

3335

2-iminoazepin-7-yl-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3336

imidazol-4-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

3337

imidazol-4-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3338

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 Ph

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3339

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 Ph

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3340

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3341

imidazol-2-ylamino-(CH.sub.2).sub.3

CH(CH.sub.3).sub.2

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3342

imidazol-2-ylamino-(CH.sub.2).sub.3

cyclopropyl

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3343

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 -

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

cyclopropyl

3344

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 COOH

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3345

imidazol-2-ylamino-(CH.sub.2).sub.3

(CH.sub.2).sub.2 NMe.sub.2

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3346

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 OMe

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3347

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 Ph

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3348

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 OH

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

3349

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

3350

imidazol-2-ylamino-(CH.sub.2).sub.3

CH(CH.sub.3).sub.2

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

3351

imidazol-2-ylamino-(CH.sub.2).sub.3

cyclopropyl

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

3352

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 -

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

cyclopropyl

3353

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 COOH

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

3354

imidazol-2-ylamino-(CH.sub.2).sub.3

(CH.sub.2).sub.2 NMe.sub.2

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

3355

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 OMe

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

3356

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 Ph

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

3357

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 OH

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

3358

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 -(1-naphthyl)

3359

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3360

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3361

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 -(1-naphthyl)

3362

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3363

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3364

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 -(1-naphthyl)

3365

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3366

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

3367

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 -(1-naphthyl)

3368

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

3369

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

__________________________________________________________________________

##STR62##

Ex. No.

R.sup.1 R.sup.9

R.sup.14 R.sup.15 MS

__________________________________________________________________________

4001

imidazol-2-ylamino-(CH.sub.2).sub.3

›H H H

4002

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHCOOCH.sub.2 Ph

4002a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHCOOCH.sub.2 Ph

4002b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 Ph

4002c

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 Ph

4003

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(2-CH.sub.3)

4004

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(3-CH.sub.3)

4005

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(4-CH.sub.3)

4006

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 (2-pyridinyl

)

4007

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.3 (3-pyridinyl

)

4010

imidazol-4-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 (2-thiazolyl

)

4015

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 (4-isoxazoly

4016

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 CH.sub.2 (2-thienyl)

4017

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 n-Bu

4018

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 i-Bu

4019

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H NHCO.sub.2 t-Bu

4020

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H NHSO.sub.2 Ph

4020a

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 Ph

4020b

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 Ph

4020c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 Ph

4020d

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 Ph

4021

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

4021a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

4021b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

4021c

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-Ph)

4021d

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-Ph)

4021e

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-Ph)

4021f

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Me.sub.2 -4-Ph)

4024

imidazol-4-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 (2-pyridyl)

4029

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 (4-isoxazolyl)

4030

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

4030a

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

4030b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

4030c

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

4031

imidazolin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-Br)

4032

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

4033

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Br)

4034

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(2-F)

4035

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.4

-(3-F)

4038

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 (1-naphthyl)

4038a

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

4038b

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-Cl.sub.2 -4-Ph)

4043

imidazol-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 -i-Bu

4044

pyridin-2-ylamino-(CH.sub.2).sub.3

H H NHSO.sub.2 -t-Bu

4045

imidazol-2-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

4046

pyridin-2-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

4047

imidazolin-2-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

4048

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

4049

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

4050

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

4051

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

4054

imidazol-4-ylamino-(CH.sub.2).sub.3

H (3,4-methylenedioxy)phenyl

4059

imidazol-2-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

4060

pyridin-2-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

4061

imidazolin-2-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

4062

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

4063

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

4064

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H 3-pyridinyl H

4065

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H 3-pyridinyl H

4068

imidazol-4-ylamino-(CH.sub.2).sub.3

H 3-pyridinyl H

4068a

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 -(1-naphthyl)

4068b

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHCO.sub.2 CH.sub.2 Ph

4068c

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4068d

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 -(1-naphthyl)

4068e

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHCO.sub.2 CH.sub.2 Ph

4068f

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4068g

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 -(1-naphthyl)

4068h

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHCO.sub.2 CH.sub.2 Ph

4068i

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4068j

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H H NHSO.sub.2 -(1-naphthyl)

4068k

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H H NHCO.sub.2 CH.sub.2 Ph

4068l

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4075

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4076

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(3-CH.sub.3)

4077

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (3-pyridinyl

)

4078

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thiazolyl

)

4079

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thienyl)

4080

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (5-isoxazoly

4081

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 n-Bu

4082

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›H NHCOPh

4083

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 Ph

4084

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 CH.sub.2 Ph

4085

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›H NHCOCH═CHPh

4086

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (3-pyridinyl)

4087

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (2-thienyl)

4088

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (cyclohexyl)

4089

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOn-Bu

4090

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCONHCH.sub.2 Ph

4091

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

4092

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

4093

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-CH.sub.3).sub.2

4094

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

4095

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (3-pyridyl)

4096

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thienyl)

4097

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

4098

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 4-(3,5-dimethyl)isox

azolyl!

4099

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Br)

4100

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-F)

4101

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

4102

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

4103

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

4104

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

4104a

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(4-pyridyl)

4104b

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-oxazolyl)

4104c

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(3-pyrazolyl)

4105

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

4105a

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyridyl)-2,6-dimethyl

4105b

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxazolyl)-2,6-dimethyl

4105c

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyrazolyl)-2,6-dimethyl

4106

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4107

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H-(4-Ph-2,6-d

imethyl-3-chloro)

4108

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

4109

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -n-Bu

4110

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

4111

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

4112

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

4113

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4114

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(3-pyridyl)

4115

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 4-(3,5-dimethyl)isox

azolyl!

4116

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Br)

4117

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-F)

4118

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

4119

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(1-naphthyl)

4120

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

4121

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

4122

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4123

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHCH.sub.2 Ph

4124

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH-n-Bu

4125

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(3-CH.sub.3)

4126

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (3-pyridinyl

)

4127

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thiazolyl

)

4128

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (4-isoxazoly

4129

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 i-Bu

4130

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›H NHCOPh

4131

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 Ph

4132

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 CH.sub.2 Ph

4133

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›H NHCOCH═CHPh · 1 of 6

4134

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (3-pyridinyl)

4135

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (2-thienyl)

4136

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOCH.sub.2 (cyclohexyl)

4137

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOn-Bu

4138

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCONHCH.sub.2 Ph

4139

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

4140

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

4141

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-CH.sub.3).sub.2

4142

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

4143

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (3-pyridyl)

4144

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thienyl)

4145

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

4146

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Br)

4147

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-F)

4148

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

4149

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

4150

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

4151

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

4151a

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(4-pyridyl)

4151b

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-oxazolyl)

4151c

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(3-pyrazolyl)

4152

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

4152a

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyridyl)-2,6-dimethyl

4152b

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxazolyl)-2,6-dimethyl

4152c

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyrazolyl)-2,6-dimethyl

4153

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4154

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

4155

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -n-Bu

4156

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

4157

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

4158

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

4159

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4160

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(3-pyridyl)

4161

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

4162

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Br)

4163

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-F)

4164

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

4165

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH)1-naphthyl)

4166

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

4167

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

4168

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4169

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHCH.sub.2 Ph

4170

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH-n-Bu

4171

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCOOCH.sub.2 Ph

4172

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(4-CH.sub.3)

4173

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.3 (3-pyridinyl

)

4173

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thiazolyl

)

4175

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thienyl)

4176

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 n-Bu

4177

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

4178

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

4179

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

4180

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

4181

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (3-pyridyl)

4182

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thienyl)

4183

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

4184

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(2-Br)

4185

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-F)

4186

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

4187

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

4188

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

4189

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

4189a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(4-pyridyl)

4189b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-oxazolyl)

4189c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(3-pyrazolyl)

4190

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2-6-dimethyl)

4190a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyridyl)-2,6-dimethyl

4190b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxazolyl)-2,6-dimethyl

4190c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyrazolyl)-2,6-dimethyl

4191

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›H NHCOCH═CHPh · 2 of 6

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4192

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

4193

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -n-Bu

4194

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

4195

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

4196

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

4197

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4198

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 4-(3,5-dimethyl)isox

azolyl!

4199

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

4200

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(1-naphthyl)

4201

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

4202

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

4203

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4204

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHCH.sub.2 Ph

4205

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6

H.sub.4 -(4-CH.sub.3)

4206

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (3-pyridinyl

)

4207

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thiazolyl

)

4208

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 (2-thienyl)

4209

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 i-Bu

4210

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

4211

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

4212

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

4213

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

4214

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (3-pyridyl)

4215

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thienyl)

4216

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

4217

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

4218

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

4218a

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-F)

4219

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

4220

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

4221

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

4222

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

4223

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

4224

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4225

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

4226

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -n-Bu

4227

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

4228

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

4229

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

4230

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4231

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

4232

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH)1-naphthyl)

4233

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

4234

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

4235

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4236

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHCH.sub.2 Ph

4237

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

4238

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

4239

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

4240

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

4241

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (4-pyridyl)

4242

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thienyl)

4243

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

4244

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

4245

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

4246

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-F)

4247

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

4248

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

4249

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

4250

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

4250a

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(4-pyridyl)

4250b

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(2-oxazolyl)

4250c

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-4-(3-pyrazolyl)

4251

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

4251a

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(3-pyridyl)-2,6-dimethyl)

4251b

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-oxazolyl)-2,6-dimethyl)

4251c

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-4-(2-pyrazolyl)-2,6-dimethyl)

4252

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4253

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H NHCOCH═CHPh · 3 of 6

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

4254

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -i-Bu

4255

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

4256

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

4257

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

4258

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4259

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

4260

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH)1-naphthyl)

4261

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

4262

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph-2,6-dimethyl)

4263

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph-2,6-dichloro)

4264

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHCH.sub.2 Ph

4265

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4266

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 i-Bu

4267

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

4268

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Me.sub.2)

4269

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-Me.sub.3)

4270

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (3-pyridyl)

4271

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-thiazolyl)

4272

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (4-isoxazolyl)

4273

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-Br)

4274

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(3-F)

4275

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.3

-(2,6-Cl.sub.2)

4276

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (2-naphthyl)

4277

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (1-naphthyl)

4278

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.4

-(4-Ph)

4279

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

4280

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4281

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 CH.sub.2 Ph

4282

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -i-Bu

4283

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHPh

4284

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-CH.sub.3)

4285

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.3

-(2,6-Me.sub.2)

4286

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4287

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH(2-naphthyl)

4288

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NH)1-naphthyl)

4289

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.4

-(4-Ph)

4290

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dimethyl)

4291

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 NHC.sub.6 H.sub.2

-(4-Ph-2,6-dichloro)

4292

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 n-Bu

4293

2-aminopyridin-6-yl-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 i-Bu

4294

2-iminoazepin-7-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

4295

imidazol-4-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 Ph

4296

2-iminoazepin-7-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (4-isoxazolyl)

4297

imidazol-4-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 (4-isoxazolyl)

4298

2-iminoazepin-7-yl-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

4299

imidazol-4-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)iso

xazolyl!

4300

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

3-pyridinyl NHSO.sub.2 Ph

4301

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

3-pyridinyl NHSO.sub.2 Ph

4302

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

(3,4-methylenedioxy)phenyl

NHSO.sub.2 Ph

4303

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

(3,4-methylenedioxy)phenyl

NHSO.sub.2 Ph

4304

imidazol-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

4305

imidazol-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4306

imidazol-2-ylamino-carbonyl-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4307

pyridin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

4308

pyridin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4309

pyridin-2-ylamino-carbonyl-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

4310

imidazolin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

4311

imidazolin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4312

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

4313

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4314

benzimidazol-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

4315

benzimidazol-2-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4316

benzimidazol-2-ylamino-carbonyl-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3).sub.3

4317

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

4318

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4319

2-iminoazepin-7-yl-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

4320

2-iminoazepin-7-yl-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4321

imidazol-4-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHSO.sub.2 Ph

4322

imidazol-4-ylamino-(CH.sub.2).sub.2

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4323

imidazol-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

4324

imidazol-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4325

pyridin-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

4326

pyridin-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4327

imidazolin-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

4328

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

4329

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

›H NHCOCH═CHPh · 4 of 6

4330

benzimidazol-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

4331

benzimidazol-2-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4332

2-aminopyridin-6-yl-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

4333

2-aminopyridin-6-yl-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4334

2-iminoazepin-7-yl-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

4335

2-iminoazepin-7-yl-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4336

imidazol-4-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHSO.sub.2 Ph

4337

imidazol-4-ylamino-(CH.sub.2).sub.4

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4338

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 Ph

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4339

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 Ph

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4340

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4341

imidazol-2-ylamino-(CH.sub.2).sub.3

CH(CH.sub.3).sub.2

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4342

imidazol-2-ylamino-(CH.sub.2).sub.3

cyclopropyl

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4343

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 -

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

cyclopropyl

4344

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 COOH

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4345

imidazol-2-ylamino-(CH.sub.2).sub.3

(CH.sub.2).sub.2 NMe.sub.2

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4346

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 OMe

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4347

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 Ph

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4348

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 OH

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,4,6-CH.sub.3)

4349

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.3

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

4350

imidazol-2-ylamino-(CH.sub.2).sub.3

CH(CH.sub.3).sub.2

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

4351

imidazol-2-ylamino-(CH.sub.2).sub.3

cyclopropyl

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

4352

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 -

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

cyclopropyl

4353

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 COOH

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

4354

imidazol-2-ylamino-(CH.sub.2).sub.3

(CH.sub.2).sub.2 NMe.sub.2

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

4355

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 OMe

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

4356

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 Ph

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

4357

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.2 CH.sub.2 OH

H NHSO.sub.2 C.sub.6 H.sub.2

-(2,6-CH.sub.3).sub.2 -4-Ph

4358

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 -(1-naphthyl)

4359

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4360

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4361

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 -(1-naphthyl)

4362

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4363

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4364

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 -(1-naphthyl)

4365

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4366

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

4367

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 -(1-naphthyl)

4368

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

CH.sub.3

H NHCO.sub.2 CH.sub.2 Ph

4369

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

CH.sub.3

H NHSO.sub.2 C.sub.6 C.sub.2

-(2,4,6-Me.sub.3)

__________________________________________________________________________

##STR63##

Ex. No.

R.sup.1 R.sup.14 R.sup.15 MS

__________________________________________________________________________

5001

imidazol-2-ylamino-(CH.sub.2).sub.3

H H

5002

pyridin-2-ylamino-(CH.sub.2).sub.3

H NHCOOCH.sub.2 Ph

5003

imidazolin-2-yl amino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

5004

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

5005

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

5006

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 (2-pyridinyl)

5007

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 (3-pyridinyl)

5010

imidazol-4-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

5015

imidazol-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 (4-isoxazolyl)

5016

pyridin-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 (2-thienyl)

5017

imidazolin-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 n-Bu

5018

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 i-Bu

5019

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 t-Bu

5020

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H NHSO.sub.2 Ph

5021

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

5024

imidazol-4-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 (2-pyridyl)

5029

imidazol-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 (4-isoxazolyl)

5030

pyridin-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)isoxazolyl!

5031

imidazolin-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(2-Br)

5032

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(3-Br)

5033

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(4-Br)

5034

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(2-F)

5035

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

5038

imidazol-4-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 (1-naphthyl)

5043

imidazol-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 -i-Bu

5044

pyridin-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 -t-Bu

5045

imidazol-2-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

5046

pyridin-2-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

5047

imidazolin-2-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

›H NHCOCH═CHPh · 5 of 6

5048

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

5049

benzimidazol-2-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

5050

2-aminopyridin-6-yl-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

5051

2-iminoazepin-7-yl-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

5054

imidazol-4-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

5059

imidazol-2-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

5060

pyridin-2-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

5061

imidazolin-2-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

5062

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

5063

benzimidazol-2-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

5064

2-aminopyridin-6-yl-(CH.sub.2).sub.3

3-pyridinyl H

5065

2-iminoazepin-7-yl-(CH.sub.2).sub.3

3-pyridinyl H

5068

imidazol-4-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

5069

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 -(1-naphthyl)

5070

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHCO.sub.2 CH.sub.2 Ph

5071

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.su

b.3)

5072

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 -(1-naphthyl)

5073

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHCO.sub.2 CH.sub.2 Ph

5074

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.su

b.3)

5075

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 -(1-naphthyl)

5076

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHCO.sub.2 CH.sub.2 Ph

5077

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.su

b.3)

5078

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H NHSO.sub.2 -(1-naphthyl)

5079

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H NHCO.sub.2 CH.sub.2 Ph

5080

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.su

b.3)

__________________________________________________________________________

##STR64##

Ex. No.

R.sup.1 R.sup.14 R.sup.15 MS

__________________________________________________________________________

6001

imidazol-2-ylamino-(CH.sub.2).sub.3

H H

6002

pyridin-2-ylamino-(CH.sub.2).sub.3

H NHCOOCH.sub.2 Ph

6003

imidazolin-2-yl amino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(2-CH.sub.3)

6004

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(3-CH.sub.3)

6005

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 C.sub.6 H.sub.4

-(4-CH.sub.3)

6006

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 (2-pyridinyl)

6007

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 (3-pyridinyl)

6010

imidazol-4-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 (2-thiazolyl)

6015

imidazol-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 (4-isoxazolyl)

6016

pyridin-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 CH.sub.2 (2-thienyl)

6017

imidazolin-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 n-Bu

6018

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 i-Bu

6019

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H NHCO.sub.2 t-Bu

6020

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H NHSO.sub.2 Ph

6021

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

6024

imidazol-4-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 (2-pyridyl)

6029

imidazol-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 (4-isoxazolyl)

6030

pyridin-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 - 4-(3,5-dimethyl)isoxazolyl!

6031

imidazolin-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(2-Br)

6032

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(3-Br)

6033

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(4-Br)

6034

2-aminopyridin-6-yl-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(2-F)

6035

2-iminoazepin-7-yl-(CH.sub.2).sub.3

H NHSO.sub.2 C.sub.6 H.sub.4 -(3-F)

6038

imidazol-4-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 (1-naphthyl)

6043

imidazol-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 -i-Bu

6044

pyridin-2-ylamino-(CH.sub.2).sub.3

H NHSO.sub.2 -t-Bu

6045

imidazol-2-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

6046

pyridin-2-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

6047

imidazolin-2-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

6048

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

6049

benzimidazol-2-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

6050

2-aminopyridin-6-yl-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

6051

2-iminoazepin-7-yl-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

6054

imidazol-4-ylamino-(CH.sub.2).sub.3

(3,4-methylenedioxy)phenyl

6059

imidazol-2-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

6060

pyridin-2-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

6061

imidazolin-2-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

6062

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

6063

benzimidazol-2-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

6064

2-aminopyridin-6-yl-(CH.sub.2).sub.3

3-pyridinyl H

6065

2-iminoazepin-7-yl-(CH.sub.2).sub.3

3-pyridinyl H

6068

imidazol-4-ylamino-(CH.sub.2).sub.3

3-pyridinyl H

6069

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 -(1-naphthyl)

6070

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHCO.sub.2 CH.sub.2 Ph

6071

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.su

b.3)

6072

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 -(1-naphthyl)

6073

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHCO.sub.2 CH.sub.2 Ph

6074

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.su

b.3)

6075

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 -(1-naphthyl)

6076

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHCO.sub.2 CH.sub.2 Ph

6077

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.su

b.3)

6078

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H NHSO.sub.2 -(1-naphthyl)

6079

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H NHCO.sub.2 CH.sub.2 Ph

6080

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.su

b.3)

__________________________________________________________________________

##STR65##

Ex. No.

R.sup.1 R.sup.10

›H NHCOCH═CHPh · 6 of 6

X.sup.1

X.sup.3

X.sup.4

R.sup.15 MS

__________________________________________________________________________

7001

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHCO.sub.2 CH.sub.2 Ph

7002

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N CH NHCO.sub.2 n-Bu

7003

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHCO.sub.2 i-Bu

7004

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH

›N CH NHCOPh

7005

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHCOCH.sub.2 Ph

7006

imidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHCOCH.sub.2 CH.sub.2 Ph

7007

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N CH

›CH NHCOCH═CHPh

7008

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHCOn-Bu

7009

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 Ph

7010

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

7011

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

7012

imidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

7013

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3)

.sub.2

7014

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub.

3).sub.3

7015

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 (2-pyridyl)

7016

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 (3-pyridyl)

7017

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N NHSO.sub.2 (4-pyridyl)

7018

imidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 (2-thienyl)

7019

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 4-(3,5-dimethyl)isoxazolyl!

7020

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2)

7021

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 (2-naphthyl)

7022

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 (1-naphthyl)

7023

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

7024

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dime

thyl)

7025

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dich

loro)

7026

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

7027

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dimethyl

7028

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dichloro

7029

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

7030

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dimethyl

7031

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dichloro

7031a

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-pyridyl)-

2,6-dimethyl

7031b

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2,

6-dimethyl

7031c

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)2,6

-dimethyl

7031d

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazolyl

)-2,6-dimethyl

7032

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 CH.sub.2 Ph

7033

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 -n-Bu

7034

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NHPh

7035

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub.

7036

imidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.su

b.3)

7037

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NH(2-naphthyl)

7038

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NH(1-naphthyl)

7039

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

7040

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

methyl)

7041

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dich

loro)

7042

imidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHCH.sub.2 Ph

7043

imidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NH-n-Bu

7044

imidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NH-i-Bu

7045

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›N CH

CH NHSO.sub.2 NH-t-Bu

7046

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHCO.sub.2 CH.sub.2 Ph

7047

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHCO.sub.2 n-Bu

7048

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHCO.sub.2 i-Bu

7049

pyridin-2-ylamino-(CH.sub.2).sub.3

H N CH

›CH NHCOPh

7050

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHCOCH.sub.2 Ph

7051

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHCOCH.sub.2 CH.sub.2 Ph

7052

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH

›N CH NHCOCH═CHPh

7053

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHCOn-Bu

7054

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 Ph

7055

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

7056

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

7057

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

7058

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3)

.sub.2

7059

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub.

3).sub.3

7060

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 (2-pyridyl)

7061

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N CH NHSO.sub.2 (3-pyridyl)

7062

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 (4-pyridyl)

7063

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 (2-thienyl)

7064

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 4-(3,5-dimethyl)isoxazolyl!

7065

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2)

7066

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 (2-naphthyl)

7067

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 (1-naphthyl)

7068

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

7069

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph-2,6-dime

thyl)

7070

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph-2,6-dich

loro)

7071

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

7072

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dimethyl

7073

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dichloro

7074

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

7075

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dimethyl

7076

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dichloro

7076a

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)-

2,6-dimethyl

7076b

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2,

6-dimethyl

7076c

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2,

6-dimethyl

7076d

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazolyl

)-2,6-dimethyl

7077

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N NHSO.sub.2 CH.sub.2 Ph

7078

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 -n-Bu

7079

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NHPh

7080

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub.

7081

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.su

b.3)

7082

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NH(2-naphthyl)

7083

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 NH(1-naphthyl)

7084

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

7085

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

methyl)

7086

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

chloro)

7087

pyridin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NHCH.sub.2 Ph

7088

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NH-n-Bu

7089

pyridin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 NH-i-Bu

7090

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NH-t-Bu

7091

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

C.sub.2 H.sub.5

›N CH

CH NHCO.sub.2 CH.sub.2 Ph

7092

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHCO.sub.2 n-Bu

7093

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHCO.sub.2 i-Bu

7094

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH

›N CH NHCOPh

7095

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHCOCH.sub.2 Ph

7096

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHCOCH.sub.2 CH.sub.2 Ph

7097

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N CH

›CH NHCOCH═CHPh

7098

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHCOn-Bu

7099

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 Ph

7100

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

7101

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

7102

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

7103

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3)

.sub.2

7104

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub.

3).sub.3

7105

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 (2-pyridyl)

7106

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 (3-pyridyl)

7107

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 (4-pyridyl)

7108

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N N CH NHSO.sub.2 (2-thienyl)

7109

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 4-(3,5-dimethyl)isoxazolyl!

7110

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2)

7111

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 (2-naphthyl)

7112

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 (1-naphthyl)

7113

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

7114

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dime

thyl)

7115

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dich

loro)

7116

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

7117

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dimethyl

7118

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dichloro

7119

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

7120

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dimethyl

7121

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dichloro

7121a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)-

2,6-dimethyl

7121b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2,

6-dimethyl

7121c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2,

6-dimethyl

7121d

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazolyl

)-2,6-dimethyl

7122

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N CH NHSO.sub.2 CH.sub.2 Ph

7123

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 -n-Bu

7124

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NHPh

7125

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub.

7126

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.su

b.3)

7127

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NH(2-naphthyl)

7128

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NH(1-naphthyl)

7129

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

7130

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

methyl)

7131

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

chloro)

7132

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHCH.sub.2 Ph

7133

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NH-n-Bu

7134

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NH-i-Bu

7135

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NH-t-Bu

7136

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHCO.sub.2 CH.sub.2 Ph

7137

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHCO.sub.2 n-Bu

7138

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHCO.sub.2 i-Bu

7139

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N CH

›CH NHCOPh

7140

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHCOCH.sub.2 Ph

7141

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHCOCH.sub.2 CH.sub.2 Ph

7142

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›N CH NHCOCH═CHPh

7143

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHCOn-Bu

7144

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 Ph

7145

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

7146

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

7147

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

7148

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3)

.sub.2

7149

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub.

3).sub.3

7150

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 (2-pyridyl)

7151

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 (3-pyridyl)

7152

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 (4-pyridyl)

7153

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 (2-thienyl)

7154

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 4-(3,5-dimethyl)isoxazolyl!

7155

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2)

7156

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 (2-naphthyl)

7157

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 (1-naphthyl)

7158

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

7159

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dime

thyl)

7160

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dich

loro)

7161

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

7162

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dimethyl

7163

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dichloro

7164

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

7165

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dimethyl

7166

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dichloro

7166a

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)-

2,6-dimethyl

7166b

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2,

6-dimethyl

7166c

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2,

6-dimethyl

7166d

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazolyl

)-2,6-dimethyl

7167

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 CH.sub.2 Ph

7168

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 -n-Bu

7169

imidazolin-2-ylamino-(CH.sub.2).sub.3

Br N CH

CH NHSO.sub.2 NHPh

7170

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub.

7171

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.su

b.3)

7172

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NH(2-naphthyl)

7173

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 NH(1-naphthyl)

7174

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

7175

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

methyl)

7176

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

chloro)

7177

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NHCH.sub.2 Ph

7178

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NH-n-Bu

7179

imidazolin-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 NH-i-Bu

7180

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NH-t-Bu

7181

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHCO.sub.2 CH.sub.2 Ph

7182

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHCO.sub.2 n-Bu

7183

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHCO.sub.2 i-Bu

7184

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH

›N CH NHCOPh

7185

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHCOCH.sub.2 Ph

7186

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHCOCH.sub.2 CH.sub.2 Ph

7187

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N CH

›CH NHCOCH═CHPh

7188

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N CH NHCOn-Bu

7189

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 Ph

7190

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

7191

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

7192

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

7193

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3)

.sub.2

7194

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub.

3).sub.3

7195

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 (2-pyridyl)

7196

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 (3-pyridyl)

7197

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 (4-pyridyl)

7198

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 (2-thienyl)

7199

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 4-(3,5-dimethyl)isoxazolyl!

7200

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2)

7201

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 (2-naphthyl)

7202

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 (1-naphthyl)

7203

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

7204

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dime

thyl)

7205

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dich

loro)

7206

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

7207

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dimethyl

7208

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dichloro

7209

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

7210

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dimethyl

7211

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dichloro

7211a

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)-

2,6-dimethyl

7211b

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2,

6-dimethyl

7211c

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2,

6-dimethyl

7211d

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazolyl

)-2,6-dimethyl

7212

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N CH NHSO.sub.2 CH.sub.2 Ph

7213

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 -n-Bu

7214

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NHPh

7215

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub.

7216

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.su

b.3)

7217

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NH(2-naphthyl)

7218

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NH(1-naphthyl)

7219

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

7220

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

methyl)

7221

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

chloro)

7222

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHCH.sub.2 Ph

7223

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NH-n-Bu

7224

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H CH

N CH NHSO.sub.2 NH-i-Bu

7225

benzimidazol-2-ylamino-(CH.sub.2).sub.3

›H N CH

CH NHSO.sub.2 NH-t-Bu

7226

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 CH.sub.2 Ph

7227

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N NHCO.sub.2 n-Bu

7228

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHCO.sub.2 i-Bu

7229

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N CH

›CH NHCOPh

7230

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHCOCH.sub.2 Ph

7231

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHCOCH.sub.2 CH.sub.2 Ph

7232

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH

›N CH NHCOCH═CHPh

7233

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N NHCOn-Bu

7234

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 Ph

7235

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

7236

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

7237

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

7238

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3)

.sub.2

7239

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub.

3).sub.3

7240

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 (2-pyridyl)

7241

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 (3-pyridyl)

7242

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N NHSO.sub.2 (4-pyridyl)

7243

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHSO.sub.2 (2-thienyl)

7244

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

›N CH

CH NHSO.sub.2 4-(3,5-dimethyl)isoxazolyl!

7245

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2)

7246

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 (2-naphthyl)

7247

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 (1-naphthyl)

7248

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

7249

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dime

thyl)

7250

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-dich

loro)

7251

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

7252

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dimethyl

7253

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)-

2,6-dichloro

7254

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

7255

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dimethyl

7256

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl)

-2,6-dichloro

7256a

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)-

2,6-dimethyl

7256b

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2,

6-dimethyl

7256c

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2,

6-dimethyl

7256d

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazolyl

)-2,6-dimethyl

7257

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N NHSO.sub.2 CH.sub.2 Ph

7258

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHSO.sub.2 -n-Bu

7259

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 NHPh

7260

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub.

7261

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.su

b.3)

7262

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 NH(2-naphthyl)

7263

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N NHSO.sub.2 NH(1-naphthyl)

7264

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

7265

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

methyl)

7266

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-di

chloro)

7267

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H N CH

CH NHSO.sub.2 NHCH.sub.2 Ph

7268

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N CH NHSO.sub.2 NH-n-Bu

7269

2-aminopyridin-6-yl-(CH.sub.2).sub.2

›H CH

N NHSO.sub.2 NH-i-Bu

7270

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHSO.sub.2 NH-t-Bu

7271

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHSO.sub.2 -(1-naphthyl)

7272

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHCO.sub.2 CH.sub.2 Ph

7273

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.sub.

7274

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHSO.sub.2 -(1-naphthyl)

7275

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHCO.sub.2 CH.sub.2 Ph

7276

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.sub.

7277

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHSO.sub.2 -(1-naphthyl)

7278

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHCO.sub.2 CH.sub.2 Ph

7279

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.sub.

7280

imidazolin-2-ylamino-(o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHSO.sub.2 -(1-naphthyl)

7281

imidazolin-2-ylamino-(o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHCO.sub.2 CH.sub.2 Ph

7282

imidazolin-2-ylamino-(o-C.sub.6 H.sub.4)-CH.sub.2

›H N CH

CH NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.sub.

__________________________________________________________________________

##STR66##

Ex.

No. R.sup.1 R.sup.9

X.sup.1

X.sup.3

X.sup.4

R.sup.15 MS

__________________________________________________________________________

8001

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCO.sub.2 CH.sub.2 Ph

8002

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH N CH NHCO.sub.2 n-Bu

8003

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCO.sub.2 i-Bu

8004

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›N CH CH NHCOPh

8005

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCOCH.sub.2 Ph

8006

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N N CH NHCOCH.sub.2 CH.sub.2 Ph

8007

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›CH CH N NHCOCHCHPh

8008

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHCOn-Bu

8009

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 Ph

8010

imidazol-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

8011

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

8012

imidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

8013

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3

).sub.2

8014

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub

.3).sub.3

8015

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (2-pyridyl)

8016

imidazol-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 (3-pyridyl)

8017

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (4-pyridyl)

8018

imidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 (2-thienyl)

8019

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

8020

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2

)

8021

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (2-naphthyl)

8022

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 (1-naphthyl)

8023

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

8024

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8025

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8026

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

8027

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dimethyl

8028

imidazol-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dichloro

8029

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

)

8030

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dimethyl

8031

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dichloro

8031a

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)

2,6-dimethyl

8031b

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2

,6-

dimethyl

8031c

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2

,6-

dimethyl

8031d

imidazol-2-ylamino-(CH.sub.2)3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazoly

l)-

2,6-dimethyl

8032

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHSO.sub.2 CH.sub.2 Ph

8033

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 -n-Bu

8034

imidazol-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 NHPh

8035

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub

.2)

8036

imidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.s

ub.3)

8037

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NH(2-naphthyl)

8038

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH N CH NHSO.sub.2 NH(1-naphthyl)

8039

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

8040

imidazol-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8041

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8042

imidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHCH.sub.2 Ph

8043

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NH-n-Bu

8044

imidazol-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHSO.sub.2 NH-i-Bu

8045

imidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NH-t-Bu

8046

pyridin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHCO.sub.2 CH.sub.2 Ph

8047

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHCO.sub.2 n-Bu

8048

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHCO.sub.2 i-Bu

8049

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›CH CH N NHCOPh

8050

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHCOCH.sub.2 Ph

8051

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHCOCH.sub.2 CH.sub.2 Ph

8052

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›N CH CH NHCOCHCHPh

8053

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCOn-Bu

8054

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 Ph

8055

pyridin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

8056

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

8057

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

8058

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3

).sub.2

8059

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub

.3).sub.3

8060

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (2-pyridyl)

8061

pyridin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 (3-pyridyl)

8062

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (4-pyridyl)

8063

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 (2-thienyl)

8064

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

8065

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2

)

8066

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (2-naphthyl)

8067

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 (1-naphthyl)

8068

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

8069

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8070

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8071

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

8072

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dimethyl

8073

pyridin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dichloro

8074

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

)

8075

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dimethyl

8076

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dichloro

8076a

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)

2,6-dimethyl

8076b

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2

,6-

dimethyl

8076c

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2

,6-

dimethyl

8076d

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazoly

l)-

2,6-dimethyl

8077

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 CH.sub.2 Ph

8078

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 -n-Bu

8079

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHPh

8080

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH N CH NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub

.2)

8081

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.s

ub.3)

8082

pyridin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 NH(2-naphthyl)

8083

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NH(1-naphthyl)

8084

pyridin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

8085

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8086

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8087

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHCH.sub.2 Ph

8088

pyridin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 NH-n-Bu

8089

pyridin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NH-i-Bu

8090

pyridin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N N CH NHSO.sub.2 NH-t-Bu

8091

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCO.sub.2 CH.sub.2 Ph

8092

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH N CH NHCO.sub.2 n-Bu

8093

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCO.sub.2 i-Bu

8094

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›N CH CH NHCOPh

8095

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCOCH.sub.2 Ph

8096

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N N CH NHCOCH.sub.2 CH.sub.2 Ph

8097

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›CH CH N NHCOCHCHPh

8098

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHCOn-Bu

8099

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 Ph

8100

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

8101

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

8102

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

8103

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3

).sub.2

8104

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub

.3).sub.3

8105

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (2-pyridyl)

8106

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 (3-pyridyl)

8107

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (4-pyridyl)

8108

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 (2-thienyl)

8109

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

8110

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2

)

8111

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (2-naphthyl)

8112

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 (1-naphthyl)

8113

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

8114

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8115

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8116

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

8117

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dimethyl

8118

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dichloro

8119

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

)

8120

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dimethyl

8121

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dichloro

8121a

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)

2,6-dimethyl

8121b

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2

,6-

dimethyl

8121c

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2

,6-

dimethyl

8121d

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazoly

l)-

2,6-dimethyl

8122

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHSO.sub.2 CH.sub.2 Ph

8123

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 -n-Bu

8124

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 NHPh

8125

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub

.2)

8126

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.s

ub.3)

8127

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NH(2-naphthyl)

8128

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH N CH NHSO.sub.2 NH(1-naphthyl)

8129

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

8130

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8131

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8132

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHCH.sub.2 Ph

8133

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NH-n-Bu

8134

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHSO.sub.2 NH-i-Bu

8135

tetrahydropyrimidin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NH-t-Bu

8136

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHCO.sub.2 CH.sub.2 Ph

8137

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHCO.sub.2 n-Bu

8138

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHCO.sub.2 i-Bu

8139

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›CH CH N NHCOPh

8140

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHCOCH.sub.2 Ph

8141

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHCOCH.sub.2 CH.sub.2 Ph

8142

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›N CH CH NHCOCHCHPh

8143

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCOn-Bu

8144

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 Ph

8145

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

8146

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

8147

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

8148

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3

).sub.2

8149

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub

.3).sub.3

8150

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (2-pyridyl)

8151

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 (3-pyridyl)

8152

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (4-pyridyl)

8153

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 (2-thienyl)

8154

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

8155

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2

)

8156

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (2-naphthyl)

8157

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 (1-naphthyl)

8158

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

8159

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8160

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8161

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

8162

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dimethyl

8163

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dichloro

8164

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

)

8165

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dimethyl

8166

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dichloro

8166a

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)

2,6-dimethyl

8166b

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2

,6-

dimethyl

8166c

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2

,6-

dimethyl

8166d

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazoly

l)-

2,6-dimethyl

8167

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 CH.sub.2 Ph

8168

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 -n-Bu

8169

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHPh

8170

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH N CH NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub

.2)

8171

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.s

ub.3)

8172

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 NH(2-naphthyl)

8173

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NH(1-naphthyl)

8174

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

8175

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8176

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8177

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHCH.sub.2 Ph

8178

imidazolin-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 NH-n-Bu

8179

imidazolin-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NH-i-Bu

8180

imidazolin-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N N CH NHSO.sub.2 NH-t-Bu

8181

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCO.sub.2 CH.sub.2 Ph

8182

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH N CH NHCO.sub.2 n-Bu

8183

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCO.sub.2 i-Bu

8184

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›N CH CH NHCOPh

8185

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHCOCH.sub.2 Ph

8186

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

N N CH NHCOCH.sub.2 CH.sub.2 Ph

8187

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

›CH CH N NHCOCHCHPh

8188

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHCOn-Bu

8189

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 Ph

8190

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

8191

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

8192

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

8193

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3

).sub.2

8194

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub

.3).sub.3

8195

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (2-pyridyl)

8196

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 (3-pyridyl)

8197

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (4-pyridyl)

8198

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 (2-thienyl)

8199

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

8200

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2

)

8201

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 (2-naphthyl)

8202

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 (1-naphthyl)

8203

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

8204

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8205

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8206

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

8207

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dimethyl

8208

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dichloro

8209

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

)

8210

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dimethyl

8211

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dichloro

8211a

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)

2,6-dimethyl

8211b

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2

,6-

dimethyl

8211c

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2

,6-

dimethyl

8211d

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazoly

l)-

2,6-dimethyl

8212

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHSO.sub.2 CH.sub.2 Ph

8213

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 -n-Bu

8214

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 NHPh

8215

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub

.2)

8216

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.s

ub.3)

8217

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NH(2-naphthyl)

8218

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH N CH NHSO.sub.2 NH(1-naphthyl)

8219

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

8220

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N CH CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8221

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8222

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H N N CH NHSO.sub.2 NHCH.sub.2 Ph

8223

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH CH N NHSO.sub.2 NH-n-Bu

8224

benzimidazol-2-ylamino-(CH.sub.2).sub.3

H CH N CH NHSO.sub.2 NH-i-Bu

8225

benzimidazol-2-ylamino-(CH.sub.2).sub.3

CH.sub.3

CH CH N NHSO.sub.2 NH-t-Bu

8226

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N CH CH NHCO.sub.2 CH.sub.2 Ph

8227

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHCO.sub.2 n-Bu

8228

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHCO.sub.2 i-Bu

8229

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

›CH CH N NHCOPh

8230

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH N CH NHCOCH.sub.2 Ph

8231

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHCOCH.sub.2 CH.sub.2 Ph

8232

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

›N CH CH NHCOCHCHPh

8233

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHCOn-Bu

8234

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 Ph

8235

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -(2-CH.sub.3)

8236

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(3-CH.sub.3)

8237

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHSO.sub.2 C.sub.6 H.sub.4 -(4-CH.sub.3)

8238

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-CH.sub.3

).sub.2

8239

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-CH.sub

.3).sub.3

8240

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 (2-pyridyl)

8241

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N CH CH NHSO.sub.2 (3-pyridyl)

8242

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 (4-pyridyl)

8243

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHSO.sub.2 (2-thienyl)

8244

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 4-(3,5-

dimethyl)isoxazolyl!

8245

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 C.sub.6 H.sub.3 -(2,6-Cl.sub.2

)

8246

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 (2-naphthyl)

8247

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 (1-naphthyl)

8248

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -(4-Ph)

8249

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8250

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8251

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

8252

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dimethyl

8253

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N CH CH NHSO.sub.2 C.sub.6 H.sub.4 -4-(4-pyridyl)

2,6-dichloro

8254

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

)

8255

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dimethyl

8256

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-oxazolyl

2,6-dichloro

8256a

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-pyridyl)

2,6-dimethyl

8256b

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(2-furyl)-2

,6-

dimethyl

8256c

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(3-furyl)-2

,6-

dimethyl

8256d

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 C.sub.6 H.sub.4 -4-(5-pyrazoly

l)-

2,6-dimethyl

8257

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 CH.sub.2 Ph

8258

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHSO.sub.2 -n-Bu

8259

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 NHPh

8260

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH N CH NHSO.sub.2 NHC.sub.6 H.sub.3 -(2,6-Me.sub

.2)

8261

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 NHC.sub.6 H.sub.2 -(2,4,6-Me.s

ub.3)

8262

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N CH CH NHSO.sub.2 NH(2-naphthyl)

8263

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH CH N NHSO.sub.2 NH(1-naphthyl)

8264

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N N CH NHSO.sub.2 NHC.sub.6 H.sub.4 -(4-Ph)

8265

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dimethyl)

8266

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

CH N CH NHSO.sub.2 NHC.sub.6 H.sub.2 -(4-Ph-2,6-

dichloro)

8267

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 NHCH.sub.2 Ph

8268

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H N CH CH NHSO.sub.2 NH-n-Bu

8269

2-aminopyridin-6-yl-(CH.sub.2).sub.2

H CH CH N NHSO.sub.2 NH-i-Bu

8270

2-aminopyridin-6-yl-(CH.sub.2).sub.2

CH.sub.3

N N CH NHSO.sub.2 NH-t-Bu

8271

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H CH CH N NHSO.sub.2 -(1-naphthyl)

8272

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H CH CH N NHCO.sub.2 CH.sub.2 Ph

8273

imidazol-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H CH CH N NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.sub

.3)

8274

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H CH CH N NHSO.sub.2 -(1-naphthyl)

8275

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H CH CH N NHCO.sub.2 CH.sub.2 Ph

8276

pyridin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H CH CH N NHSO.sub.2 C.sub.6 H.sub.2 -(2,4,6-Me.sub

.3)

8277

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H CH CH N NHSO.sub.2 -(1-naphthyl)

8278

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H CH CH N NHCO.sub.2 CH.sub.2 Ph

8279

imidazolin-2-ylamino-CH.sub.2 (o-C.sub.6 H.sub.4)

H CH CH N NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.sub

.3)

8280

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H CH CH N NHSO.sub.2 -(1-naphthyl)

8281

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H CH CH N NHCO.sub.2 CH.sub.2 Ph

8282

imidazolin-2-ylamino-(m-C.sub.6 H.sub.4)

H CH CH N NHSO.sub.2 C.sub.6 C.sub.2 -(2,4,6-Me.sub

.3)

__________________________________________________________________________

Claims

16 · 5 independent · depth 2

16 granted claims

›1.independentA compound of Formula Ia: ##STR67## and pharmaceutically acceptable salt forms thereof, wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are independen…+4

A compound of Formula Ia: ##STR67## and pharmaceutically acceptable salt forms thereof, wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are independently selected from nitrogen or carbon provided that at least two of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are carbon; R.sup.1 is selected from: ##STR68## A and B are independently --CH.sub.2 --, --O--, --N(R.sup.2)--, or --C(.dbd.O)--; A.sup.1 and B.sup.1 are independently --CH.sub.2 -- or --N(R.sup.3)--; D is --N(R.sup.2)--, --O--, --S--, --C(.dbd.O)-- or --SO.sub.2 --; E--F is --C(R.sup.4).dbd.C(R.sup.5)--, --N.dbd.C(R.sup.4)--, --C(R.sup.4).dbd.N--, or --C(R.sup.4).sub.2 C(R.sup.5).sub.2 --; J, K, L and M are independently selected from --C(R.sup.4)--, --C(R.sup.5)-- or --N--, provided that at least one of J, K, L and M is not --N--; R.sup.2 is selected from: H, C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl; (C.sub.1 -C.sub.6 alkyl)aminocarbonyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)carbonyl, heteroarylcarbonyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)darbonyl-, arylcarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl, arylsulfonyl, aryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, aryloxycarbonyl, or aryl(C.sub.1 -C.sub.6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, CF.sub.3, and nitro; R.sup.3 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.4 and R.sup.5 are independently selected from: H, C.sub.1 -C.sub.4 alkoxy, NR.sup.2 R.sup.3, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl (C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)carbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl, arylcarbonyl, or alternatively, when substituents on adjacent atoms, R.sup.4 and R.sup.5 can be taken together with the carbon atoms to which they are attached to form a 5-7 membered carbocyclic or 5-7 membered heterocyclic aromatic or non-aromatic ring system, said carbocyclic or heterocyclic ring being optionally substituted with 0-2 groups selected from: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, cyano, amino, CF.sub.3, or NO.sub.2 ; U is selected from: --(CH.sub.2).sub.n --, --(CH.sub.2).sub.n (CR.sup.7 .dbd.CR.sup.8) (CH.sub.2).sub.m --, --(CH.sub.2).sub.n (C.tbd.C) (CH.sub.2).sub.m --, --(CH.sub.2).sub.t Q(CH.sub.2).sub.m --, --(CH.sub.2).sub.n O(CH.sub.2).sub.m --, --CH.sub.2).sub.n N(R.sup.6)(CH.sub.2).sub.m --, --(CH.sub.2).sub.n C(.dbd.O)(CH.sub.2).sub.m --, --(CH.sub.2).sub.n (C.dbd.O)N(R.sup.6)(CH.sub.2).sub.m-- --(CH.sub.2).sub.n N(R.sup.6)(C.dbd.O)(CH.sub.2).sub.m --, or --(CH.sub.2).sub.n S(O).sub.p (CH.sub.2).sub.m --; wherein one or more of the methylene groups in U is optionally substituted with R.sup.7 ; Q is selected from 1,2-cycloalkylene, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, 2,4-pyridinylene, or 3,4-pyridazinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 and R.sup.8 are independently selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.0 -C.sub.6 alkyl)-; R.sup.10 is selected from: H, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, N(R.sup.6).sub.2, halogen, NO.sub.2, CN, CF.sub.3, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, --SO.sub.2 R.sup.17, --SO.sub.2 NR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.6 alkenyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.1 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, aryl substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from H, halogen, CF.sub.3, CN, NO.sub.2, hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is selected from: --(C(R.sup.12).sub.2).sub.q C(.dbd.O)N(R.sup.13)--, or C(.dbd.O)--N(R.sup.13)--(C(R.sup.12).sub.2).sub.q --; X is --C(R.sup.12)(R.sup.14)--C(R.sup.12)(R.sup.15)--; or alternatively, W and X can be taken together to be ##STR69## R.sup.12 is selected from H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.10 cycloalkylalkyl, (C.sub.1 -C.sub.4 alkyl)carbonyl, aryl, or aryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.13 is selected from H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkylmethyl, or aryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.14 is selected from: H, C.sub.1 -C.sub.6 alkylthio(C.sub.1 -C.sub.6 alkyl)-, aryl(C.sub.1 -C.sub.10 alkylthioalkyl)-, aryl(C.sub.1 -C.sub.10 alkoxyalkyl)-, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, or CONR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-1 R.sup.16 or 0-2 R.sup.11 ; R.sup.15 is selected from: H, R.sup.16, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 alkylaminoalkyl, C.sub.1 -C.sub.10 dialkylaminoalkyl, (C.sub.1 -C.sub.10 alkyl)carbonyl, aryl(C.sub.0 -C.sub.6 alkyl)carbonyl, C.sub.1 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, SO.sub.2 R.sup.17, or SO.sub.2 NR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-2 R.sup.11 ; Y is selected from: --COR.sup.19, --SO.sub.3 H, --PO.sub.3 H, tetrazolyl, --CONHNHSO.sub.2 CF.sub.3, --CONHSO.sub.2 R.sup.17, --CONHSO.sub.2 NHR.sup.17, --NHCOCF.sub.3, --NHCONHSO.sub.2 R.sup.17, --NHSO.sub.2 R.sup.17, --OP).sub.3 H.sub.2, --OSO.sub.3 H, --PO.sub.3 H.sub.2, --SO.sub.3 H, --SO.sub.2 NHCOR.sup.17, --SO.sub.2 NHCO.sub.2 R.sup.17, ##STR70## R.sup.16 is selected from: --N(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R--R.sup.17, or --N(R.sup.20)SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.18 is selected from: H, --C(.dbd.O)--O--R.sup.17, --C(.dbd.O)--R.sup.17, --C(.dbd.O)--NH--R.sup.17, --SO.sub.2 --R.sup.17, or --SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.19 is selected from: hydroxy, C.sub.1 -C.sub.10 alkyloxy, C.sub.3 -C.sub.11 cycloalkyloxy, aryloxy, aryl(C.sub.1 -C.sub.6 alkoxy)-, C.sub.3 -C.sub.10 alkylcarbonyloxyalkyloxy, C.sub.3 -C.sub.10 alkoxycarbonyloxyalkyloxy, C.sub.2 -C.sub.10 alkoxycarbonylalkyloxy, C.sub.5 -C.sub.10 cycloalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonylalkyloxy, C.sub.7 -C.sub.11 aryloxycarbonylalkyloxy, C.sub.8 -C.sub.12 aryloxycarbonyloxyalkyloxy, C.sub.8 -C.sub.12 arylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 alkoxyalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 (5-alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C.sub.10 -C.sub.14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R.sup.11)(R.sup.12)N--(C.sub.1 -C.sub.10 alkoxy)-; R.sup.20 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl (C.sub.1 -C.sub.6 alkyl)-; R.sup.21 is selected from: COOH or NR.sup.6.sub.2 ; m is 0-4; n is 0-4; t is 0-4; p is 0-2; q is 0-2; and r is 0-2; with the following provisos: (1) t, n, m and q are chosen such that the number of atoms connecting R.sup.1 and Y is in the range of 10-14; and (2) n and m are chosen such that the value of n plus m is greater than one unless U is --(CH.sub.2).sub.t Q(CH.sub.2).sub.m --.

›2.↳ 1A compound of claim 1 of the Formula Ia: ##STR71## and pharmaceutically acceptable salt forms thereof, wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4…d2

A compound of claim 1 of the Formula Ia: ##STR71## and pharmaceutically acceptable salt forms thereof, wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are independently selected from nitrogen or carbon provided that at least two of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are carbon; R.sup.1 is selected from: ##STR72## A and B are independently --CH.sub.2 --, --O--, --N(R.sup.2)--, or --C(.dbd.O)--; A.sup.1 and B.sup.1 are independently --CH.sub.2 -- or --N(R.sup.3)--; D is --N(R.sup.2)--, --O--, --S--, --C(.dbd.)-- or --SO.sub.2 --; E--F is --C(R.sup.4).dbd.C(R.sup.5)--, --N.dbd.C(R.sup.4)--, --C(R.sup.4).dbd.N--, or --C(R.sup.4).sub.2 C(R.sup.5).sub.2 --; J, K, L and M are independently selected from --C(R.sup.4)--, --C(R.sup.5)-- or --N--, provided that at least one of J, K, L and M is not --N--; R.sup.2 is selected from: H, C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl, C.sub.1 -C.sub.6 alkylaminocarbonyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)carbonyl, heteroarylcarbonyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)carbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, aryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, aryloxycarbonyl, or aryl(C.sub.1 -C.sub.6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, CF.sub.3, and nitro; R.sup.3 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl (C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.4 and R.sup.5 are independently selected from: H, C.sub.1 -C.sub.4 alkoxy, NR.sup.2 R.sup.3, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, C.sub.2 -C.sub.7 alkylcarbonyl, arylcarbonyl or alternatively, when substituents on adjacent atoms, R.sup.4 and R.sup.5 can be taken together with the carbon atoms to which they are attached to form a 5-7 membered carbocyclic or 5-7 membered heterocyclic aromatic or non-aromatic ring system, said carbocyclic or heterocyclic ring being optionally substituted with 0-2 groups selected from: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, cyano, amino, CF.sub.3, or NO.sub.2 ; U is selected from: --(CH.sub.2).sub.n --, --(CH.sub.2).sub.n (CR.sup.7 .dbd.CR.sup.8)(CH.sub.2).sub.m --, --(CH.sub.2).sub.t Q(CH.sub.2).sub.m --, --(CH.sub.2).sub.n O(CH.sub.2).sub.m --, --(CH.sub.2).sub.n N(R.sup.6)(CH.sub.2).sub.m --, --(CH.sub.2).sub.n C(.dbd.O)(CH.sub.2).sub.m --, or --(CH.sub.2).sub.n S(O).sub.p (CH.sub.2).sub.m --; wherein one or more of the methylene groups in U is optionally substituted with R.sup.7 ; Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 and R.sup.8 are independently selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.0 -C.sub.6 alkyl)-; R.sup.10 is selected from: H, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, N(R.sup.6).sub.2, halogen, NO.sub.2, CN, CF.sub.3, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, --SO.sub.2 R.sup.17, --SO.sub.2 NR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.6 alkenyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, aryl substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from: H, halogen, CF.sub.3, CN, NO.sub.2 , hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is --C(.dbd.O)--N(R.sup.13)--(C(R.sup.12).sub.2).sub.2).sub.q --; X is --C(R.sup.12)(R.sup.14)--C(R.sup.12)(R.sup.15)--; alternatively, W and X can be taken together to be ##STR73## R.sup.12 is H or C.sub.1 -C.sub.6 alkyl; R.sup.13 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkylmethyl, or aryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.14 is selected from: H, C.sub.1 -C.sub.6 alkylthioalkyl, aryl(C.sub.1 -C.sub.10 alkylthioalkyl)-, aryl(C.sub.1 -C.sub.10 alkoxyalkyl)-, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, or CONR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be substituted independently with 0-1 R.sup.16 or 0-2 R.sup.11 ; R.sup.15 is selected from: H, R.sup.16, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 alkylaminoalkyl, C.sub.1 -C.sub.10 dialkylaminoalkyl, C.sub.1 -C.sub.10 alkylcarbonyl, aryl(C.sub.0 -C.sub.6 alkyl)carbonyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, SO.sub.2 R.sup.17 or SO.sub.2 NR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be substituted independently with 0-2 R.sup.11 ; Y is selected from: ##STR74## R.sup.16 is selected from: --N(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.18 is selected from: H, --C(.dbd.O)--O--R.sup.17, --C(.dbd.O)--R.sup.17, --C(.dbd.O)--NH--R.sup.17, --SO.sub.2 --R.sup.17, or --SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.19 is selected from: hydroxy, C.sub.1 -C.sub.10 alkyloxy, C.sub.3 -C.sub.11 cycloalkyloxy, C.sub.6 -C.sub.10 aryloxy, C.sub.7 -C.sub.11 aralkyloxy, C.sub.3 -C.sub.10 alkylcarbonyloxyalkyloxy, C.sub.3 -C.sub.10 alkoxycarbonyloxyalkyloxy, C.sub.2 -C.sub.10 alkoxycarbonylalkyloxy, C.sub.5 -C.sub.10 cycloalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonylalkyloxy, C.sub.7 -C.sub.11 aryloxycarbonylalkyloxy, C.sub.8 -C.sub.12 aryloxycarbonyloxyalkyloxy, C.sub.8 -C.sub.12 arylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 alkoxyalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 (5-alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C.sub.10 -C.sub.14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R.sup.11)(R.sup.12)N--(C.sub.0 -C.sub.10 alkoxy)-; R.sup.20 selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; m is 0-4; n is 0-4; p is 0-2; q is 0-2; t is 0-4; and r is 0-2.

›3.↳ 1A compound of claim 1 of the Formula IIa or IIb: ##STR75## and pharmaceutically acceptable salt forms thereof wherein: X.sub.1 and X.sub.3 are indepen…d2

A compound of claim 1 of the Formula IIa or IIb: ##STR75## and pharmaceutically acceptable salt forms thereof wherein: X.sub.1 and X.sub.3 are independently selected from nitrogen or carbon; R.sup.1 is selected from: ##STR76## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH.sub.2, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.6 alkyl, and C.sub.3 -C.sub.7 cycloalkyl; U is --(CH.sub.2).sub.n --, --(CH.sub.2).sub.t Q(CH.sub.2).sub.m -- or --C(.dbd.O)(CH.sub.2).sub.n-1 --, wherein one of the methylene groups is optionally substituted with R.sup.7 ; Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 is selected from: C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl), heteroaryl, or heteroaryl(C.sub.1 -C.sub.6 alkyl); R.sup.10 is selected from: H, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, halogen, CO.sub.2 R.sup.17, CONR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from: H, halogen, CF.sub.3, CN, NO.sub.2, hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21 aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is --C(.dbd.O)--N(R.sup.13)--; X is --CH(R.sup.14)--CH(R.sup.15)--; R.sup.13 is H or CH.sub.3 ; R.sup.14 is selected from: H, C.sub.1 -C.sub.10 alkyl, aryl, or heteroaryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.15 is H or R.sup.16 ; Y is --COR.sup.19 ; R.sup.16 is selected from: --NH(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --N(R.sup.20)R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.19 is selected from: hydroxy, C.sub.1 -C.sub.10 alkoxy, methylcarbonyloxymethoxy-, ethylcarbonyloxymethoxy-, t-butylcarbonyloxymethoxy-, cyclohexylcarbonyloxymethoxy-, 1-(methylcarbonyloxy)ethoxy-, 1-(ethylcarbonyloxy)ethoxy-, 1-(t-butylcarbonyloxy)ethoxy-, 1-(cyclohexylcarbonyloxy)ethoxy-, i-propyloxycarbonyloxymethoxy-, t-butyloxycarbonyloxymethoxy-, 1-(i-propyloxycarbonyloxy)ethoxy-, 1-(cyclohexyloxycarbonyloxy)ethoxy-, 1-(t-butyloxycarbonyloxy)ethoxy-, dimethylaminoethoxy-, diethylaminoethoxy-, (5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or 1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-; R.sup.20 is H or CH.sub.3 ; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; m is 0 or 1; n is 1-4; and t is 0 or 1.

›4.↳ 1A compound of claim 1 of the Formula IIa or IIb: ##STR77## and pharmaceutically acceptable salt forms thereof wherein: X.sub.1 and X.sub.3 are indepen…d2

A compound of claim 1 of the Formula IIa or IIb: ##STR77## and pharmaceutically acceptable salt forms thereof wherein: X.sub.1 and X.sub.3 are independently selected from nitrogen or carbon, provided that at least one of X.sub.1 and X.sub.3 is carbon; R.sup.1 is selected from: ##STR78## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH.sub.2, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.6 alkyl, and C.sub.3 -C.sub.7 cycloalkyl; U is --(CH.sub.2).sub.n --, --(CH.sub.2).sub.t Q(CH.sub.2).sub.m -- or --C(.dbd.O)(CH.sub.2).sub.n-1, wherein one of the methylene groups is optionally substituted with R.sup.7 ; Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3 4-pyridinylene, or 2,4-pyridinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 is selected from: C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl), heteroaryl, or heteroaryl(C.sub.1 -C.sub.6 alkyl); R.sup.10 is selected from: H, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, halogen, CO.sub.2 R.sup.17, CONR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from: H, halogen, CF.sub.3, CN, NO.sub.2, hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21 aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is --C(.dbd.O)--N(R.sup.13)--; W is --C(.dbd.O)--N(R.sup.13)--; X is --CH(R.sup.14)--CH(R.sup.15)--; R.sup.13 is H or CH.sub.3 ; R.sup.14 is selected from: H, C.sub.1 -C.sub.10 alkyl, aryl, or heteroaryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.15 is H or R.sup.16 ; Y is --COR.sup.19 ; R.sup.16 is selected from: --N(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.19 is selected from: hydroxy, C.sub.1 -C.sub.10 alkoxy, methylcarbonyloxymethoxy-, ethylcarbonyloxymethoxy-, t-butylcarbonyloxymethoxy-, cyclohexylcarbonyloxymethoxy-, 1-(methylcarbonyloxy)ethoxy-, 1-(ethylcarbonyloxy)ethoxy-, 1-(t-butylcarbonyloxy)ethoxy-, 1-(cyclohexylcarbonyloxy)ethoxy-, i-propyloxycarbonyloxymethoxy-, t-butyloxycarbonyloxymethoxy-, 1-(i-propyloxycarbonyloxy)ethoxy-, 1-(cyclohexyloxycarbonyloxy)ethoxy-, 1-(t-butyloxycarbonyloxy)ethoxy-, dimethylaminoethoxy-, diethylaminoethoxy-, (5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or 1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-; R.sup.20 is H or CH.sub.3 ; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; m is 0 or 1; n is 1-4; and t is 0 or 1.

›5.↳ 1A compound of claim 1 of Formula Ia and enantiomeric or diasteriomeric forms thereof, and mixtures of enantiomeric or diasteriomeric forms thereof, an…d2

A compound of claim 1 of Formula Ia and enantiomeric or diasteriomeric forms thereof, and mixtures of enantiomeric or diasteriomeric forms thereof, and pharmaceutically acceptable salt forms thereof, selected from the group consisting of: 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzylox ycarbonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,4,6-tr imethylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzenes ulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dich lorobenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(3,5-dime thylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dime thylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dime thyl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(4-phenyl benzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(b enzyloxycarbonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2 ,4,6-trimethylbenzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(b enzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2 ,6-dichlorobenzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(3 ,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2 ,6-dimethylbenzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2 ,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(4 -phenylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzyloxyc arbonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,4,6-trim ethylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzenesul fonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dichlo robenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(3,5-dimeth ylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimeth ylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimeth yl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(4-phenylbe nzenesulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzyloxyca rbonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,4,6-trime thylbenzenesulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(benzenesulf onylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dichlor obenzenesulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(3,5-dimethy lisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimethy lbenzenesulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(2,6-dimethy l-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-5-ylcarbonylamino!-2-(4-phenylben zenesulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzylox ycarbonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,4,6-tr imethylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzenes ulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dich lorobenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(3,5-dime thylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dime thylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dime thyl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazolin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(4-phenyl benzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(b enzyloxycarbonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2 ,4,6-trimethylbenzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(b enzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2 ,6-dichlorobenzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(3 ,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2 ,6-dimethylbenzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2 ,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(4 -phenylbenzenesulfonylamino)propionic acid, 3-1-›3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzyloxyca rbonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,4,6-trim ethylbenzenesulfonylamino)propionic acid, 3-1-›3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzenesulf onylamino)propionic acid, 3-1-›3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dichlor obenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(3,5-dimeth ylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimeth ylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimeth yl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-›3-(imidazol-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(4-phenylbe nzenesulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzyloxyca rbonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,4,6-trime thylbenzenesulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(benzenesulf onylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dichlor obenzenesulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(3,5-dimethy lisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimethy lbenzenesulfonylamino)propionic acid, 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(2,6-dimethy l-4-phenylbenzenesulfonylamino)propionic acid, and 3-›1-›3-(pyridin-2-ylamino)propyl!indazol-4-ylcarbonylamino!-2-(4-phenylben zenesulfonylamino)propionic acid; and ester forms thereof, said ester being selected from the group consisting of: methyl, ethyl, isopropyl, n-butyl, isobutyl, benzyl, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, tert-butylcarbonyloxymethyl, cyclohexylcarbonyloxymethyl, tert-butyloxycarbonyloxymethyl, dimethylaminoethyl, diethylaminoethyl, morpholinoethyl, pyrrolidinoethyl, and trimethylammonioethyl.

›6.independentA compound of Formula Ib: ##STR79## and pharmaceutically acceptable salt forms thereof, wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are independen…+4

A compound of Formula Ib: ##STR79## and pharmaceutically acceptable salt forms thereof, wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are independently selected from nitrogen or carbon provided that at least two of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are carbon; R.sup.1 is selected from: ##STR80## A and B are independently --CH.sub.2 --, --O--, --N(R.sup.2)--, or --C(.dbd.O)--; A.sup.1 and B.sup.1 are independently --CH.sub.2 -- or --N(R.sup.3)--; D is --N(R.sup.2)--, --O--, --S--, --C(.dbd.O)-- or --SO.sub.2 --; E--F is --C(R.sup.4).dbd.C(R.sup.5)--, --N.dbd.C(R.sup.4)--, --C(R.sup.4).dbd.N--, or --C(R.sup.4).sub.2 C(R.sup.5).sub.2 --; J, K, L and M are independently selected from: --C(R.sup.4)--, --C(R.sup.5)-- or --N--, provided that at least one of J, K, L and M is not --N--; R.sup.2 is selected from: H, C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl; (C.sub.1 -C.sub.6 alkyl)aminocarbonyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)carbonyl, heteroarylcarbonyl, aryl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyl, or arylcarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl, arylsulfonyl, aryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, aryloxycarbonyl, or aryl(C.sub.1 -C.sub.6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, CF.sub.3, and nitro; R.sup.3 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.4 and R.sup.5 are independently selected from: H, C.sub.1 -C.sub.4 alkoxy, NR.sup.2 R.sup.3, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)carbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl, arylcarbonyl, or alternatively, when substituents on adjacent atoms, R.sup.4 and R.sup.5 can be taken together with the carbon atoms to which they are attached to form a 5-7 membered carbocyclic or 5-7 membered heterocyclic aromatic or non-aromatic ring system, said carbocyclic or heterocyclic ring being optionally substituted with 0-2 groups selected from: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, cyano, amino, CF.sub.3, or NO.sub.2 ; U is selected from: --(CH.sub.2).sub.n --, --(CH.sub.2).sub.n (CR.sup.7 .dbd.CR.sup.8)(CH.sub.2).sub.m -- --(CH.sub.2).sub.n (C.tbd.C)(CH.sub.2).sub.m -- --(CH.sub.2).sub.t Q(CH.sub.2).sub.m -- --(CH.sub.2).sub.n O(CH.sub.2).sub.m --, --(CH.sub.2).sub.n N(R.sup.6)(CH.sub.2).sub.m --, --(CH.sub.2).sub.n C(.dbd.O)(CH.sub.2).sub.m --, --(CH.sub.2).sub.n (C.dbd.O)N(R.sup.6)(CH.sub.2).sub.m -- --(CH.sub.2).sub.n N(R.sup.6)(C.dbd.O)(CH.sub.2).sub.m --, or --(CH.sub.2).sub.n S(O).sub.p (CH.sub.2).sub.m --; wherein one of the methylene groups is optionally substituted with R.sup.7 ; Q is selected from: 1,2-cycloalkylene, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, 2,4-pyridinylene, or 3,4-pyridazinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 and R.sup.8 are independently selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.0 -C.sub.6 alkyl)-; R.sup.9 is selected from: H, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, --SO.sub.2 R.sup.17, --SO.sub.2 NR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.6 alkenyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, aryl substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from H, halogen, CF.sub.3, CN, N).sub.2, hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is selected from: --(C(R.sup.12).sub.2).sub.q C(.dbd.O)N(R.sup.13)--, or --C(.dbd.O)--N(R.sup.13)--(C(R.sup.12).sub.2).sub.q --; X is --C(R.sup.12)(R.sup.14)--C(R.sup.12)(R.sup.15)--; or alternatively, W and X can be taken together to be ##STR81## R.sup.12 is selected from: H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.10 cycloalkylalkyl, (C.sub.1 -C.sub.4 alkyl)carbonyl, aryl, or aryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.13 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkylmethyl, or aryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.14 is selected from: H, C.sub.1 -C.sub.6 alkylthio(C.sub.1 -C.sub.6 alkyl)-, aryl(C.sub.1 -C.sub.10 alkylthioalkyl)-, aryl(C.sub.1 -C.sub.10 alkoxyalkyl)-, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, or CONR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-1 R.sup.16 or 0-2 R.sup.11 ; R.sup.15 is selected from: H, R.sup.16, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 alkylaminoalkyl, C.sub.1 -C.sub.10 dialkylaminoalkyl, (C.sub.1 -C.sub.10 alkyl)carbonyl, aryl(C.sub.0 -C.sub.6 alkyl)carbonyl, C.sub.1 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkynyl ,C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17 C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, SO.sub.2 R.sup.17, or SO.sub.2 NR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-2 R.sup.11 ; Y is selected from: --COR.sup.19, --SO.sub.3 H, --PO.sub.3 H, tetrazolyl, --CONHNHSO.sub.2 CF.sub.3, --CONHSO.sub.2 R.sup.17, --CONHSO.sub.2 NHR.sup.17, --NHCOCF.sub.3, --NHCONHSO.sub.2 R.sup.17, --NHSO.sub.2 R.sup.17, --OPO.sub.3 H.sub.2, --OSO.sub.3 H, --PO.sub.3 H.sub.2, --SO.sub.3 H, --SO.sub.2 NHCOR.sup.17, --SO.sub.2 NHCO.sub.2 R.sup.17 ##STR82## R.sup.16 is selected from: --N(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.18 is selected from: H, --C(.dbd.O)--O--R.sup.17, --C(.dbd.0)--R.sup.17, --C(.dbd.O)--NH--R.sup.17, --SO.sub.2 --R.sup.17, or --SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.19 is selected from hydroxy, C.sub.1 -C.sub.10 alkyloxy, C.sub.3 -C.sub.11 cycloalkyloxy, aryloxy, aryl(C.sub.1 -C.sub.6 alkoxy)-, C.sub.3 -C.sub.10 alkylcarbonyloxyalkyloxy, C.sub.3 -C.sub.10 alkoxycarbonyloxyalkyloxy, C.sub.2 -C.sub.10 alkoxycarbonylalkyloxy, C.sub.5 -C.sub.10 cycloalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonylalkyloxy, C.sub.7 -C.sub.11 aryloxycarbonylalkyloxy, C.sub.8 -C.sub.12 aryloxycarbonyloxyalkyloxy, C.sub.8 -C.sub.12 arylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 alkoxyalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 (5-alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C.sub.10 -C.sub.14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R.sup.11)(R.sup.12)N--(C.sub.1 -C.sub.10 alkoxy)-; R.sup.20 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; m is 0-4; n is 0-4; t is 0-4; p is 0-2; q is 0-2; and r is 0-2; with the following provisos: (1) t, n, m and q are chosen such that the number of atoms connecting R.sup.1 and Y is in the range of 10-14; and (2) n and m are chosen such that the value of n plus m is greater than one unless U is --(CH.sub.2).sub.t Q(CH.sub.2).sub.m --.

›7.↳ 6A compound of claim 6 of Formula Ib: ##STR83## and pharmaceutically acceptable salt forms thereof, wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are…d2

A compound of claim 6 of Formula Ib: ##STR83## and pharmaceutically acceptable salt forms thereof, wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are independently selected from nitrogen or carbon provided that at least two of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are carbon; R.sup.1 is selected from: ##STR84## A and B are independently --CH.sub.2 --, --O--, --N(R.sup.2)--, or --C(.dbd.O)--; A.sup.1 and B.sup.1 are independently --CH.sub.2 -- or --N(R.sup.3)--; D is --N(R.sup.2)--, --O--, --S--, --C(.dbd.O)-- or --SO.sub.2 --; E--F is --C(R.sup.4).dbd.C(R.sup.5)--, --N.dbd.C(R.sup.4)--, --C(R.sup.4).dbd.N--, or --C(R.sup.4).sub.2 C(R.sup.5).sub.2 --; J, K, L and M are independently selected from --C(R.sup.4)--, --C(R.sup.5)-- or --N--, provided that at least one of J, K, L and M is not --N--; R.sup.2 is selected from: H, C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl, C.sub.1 -C.sub.6 alkylaminocarbonyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)carbonyl, heteroarylcarbonyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)carbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, aryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, aryloxycarbonyl, aryl(C.sub.1 -C.sub.6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, CF.sub.3, and nitro; R.sup.3 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.4 and R.sup.5 are independently selected from: H, C.sub.1 -C.sub.4 alkoxy, NR.sup.2 R.sup.3, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, C.sub.2 -C.sub.7 alkylcarbonyl, arylcarbonyl or alternatively, when substituents on adjacent atoms, R.sup.4 and R.sup.5 can be taken together with the carbon atoms to which they are attached to form a 5-7 membered carbocyclic or 5-7 membered heterocyclic aromatic or non-aromatic ring system, said carbocyclic or heterocyclic ring being optionally substituted with 0-2 groups selected from: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, cyano, amino, CF.sub.3, or NO.sub.2 ; U is selected from: --(CH.sub.2).sub.n --, --(CH.sub.2).sub.n (CR.sup.7 .dbd.CR.sup.8)(CH.sub.2).sub.m -- --(CH.sub.2).sub.t Q(CH.sub.2).sub.m --, --(CH.sub.2).sub.n O(CH.sub.2).sub.m --, --(CH.sub.2).sub.n N(R.sup.6)(CH.sub.2).sub.m --, --(CH.sub.2).sub.n C(.dbd.O)(CH.sub.2).sub.m --, or --(CH.sub.2).sub.n S(O).sub.p (CH.sub.2).sub.m --; wherein one of the methylene groups is optionally substituted with R.sup.7 ; Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 and R.sup.8 are independently selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.0 -C.sub.6 alkyl)-; R.sup.9 is selected from: H, CO.sub.2 R.sup.17 C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, --SO.sub.2 R.sup.17, --SO.sub.2 NR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.6 alkenyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, aryl substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from: H, halogen, CF.sub.3, CN, NO.sub.2, hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is --C(.dbd.O)--N(R.sup.13)--(C(R.sup.12).sub.2).sub.q --; X is --C(R.sup.12)(R.sup.14)--C(R.sup.12)(R.sup.15)--; alternatively, W and X can be taken together to be ##STR85## R.sup.12 is H or C.sub.1 -C.sub.6 alkyl; R.sup.13 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkylmethyl, or aryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.14 is selected from: H, C.sub.1 -C.sub.6 alkylthioalkyl, aryl(C.sub.1 -C.sub.10 alkylthioalkyl)-, aryl(C.sub.1 -C.sub.10 alkoxyalkyl)-, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, or CONR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-1 R.sup.16 or 0-2 R.sup.11 ; R.sup.15 is selected from: H, R.sup.16, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 alkylaminoalkyl, C.sub.1 -C.sub.10 dialkylaminoalkyl, C.sub.1 -C.sub.10 alkylcarbonyl, aryl(C.sub.0 -C.sub.6 alkyl)carbonyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, SO.sub.2 R.sup.17, or SO.sub.2 NR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-2 R.sup.11 ; Y is selected from: ##STR86## R.sup.16 is selected from: --N(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.18 is selected from: H, --C(.dbd.O)--O--R.sup.17, --C(.dbd.O)--R.sup.17, --C(.dbd.O)--NH--R.sup.17, --SO.sub.2 --R.sup.17, or --SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.19 is selected from hydroxy, C.sub.1 -C.sub.10 alkyloxy, C.sub.3 -C.sub.11 cycloalkyloxy, C.sub.6 -C.sub.10 aryloxy, C.sub.7 -C.sub.11 aralkyloxy, C.sub.3 -C.sub.10 alkylcarbonyloxyalkyloxy, C.sub.3 -C.sub.10 alkoxycarbonyloxyalkyloxy, C.sub.2 -C.sub.10 alkoxycarbonylalkyloxy, C.sub.5 -C.sub.10 cycloalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonylalkyloxy, C.sub.7 -C.sub.11 aryloxycarbonylalkyloxy, C.sub.8 -C.sub.12 aryloxycarbonyloxyalkyloxy, C.sub.8 -C.sub.12 arylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 alkoxyalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 (5-alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C.sub.10 -C.sub.14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R.sup.11)(R.sup.12)N-(C.sub.1 -C.sub.10 alkoxy)-; R.sup.20 selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; m is 0-4; n is 0-4; t is 0-4; p is 0-2; q is 0-2; and r is 0-2.

›8.↳ 6A compound of claim 6 of the Formula IIc or IId: ##STR87## and pharmaceutically acceptable salt forms thereof, wherein: X.sub.1 and X.sub.3 are indepe…d2

A compound of claim 6 of the Formula IIc or IId: ##STR87## and pharmaceutically acceptable salt forms thereof, wherein: X.sub.1 and X.sub.3 are independently selected from nitrogen or carbon; R.sup.1 is selected from: ##STR88## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH.sub.2, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.6 alkyl, and C.sub.3 -C.sub.7 cycloalkyl; U is --(CH.sub.2).sub.n --, --(CH.sub.2).sub.t Q(CH.sub.2).sub.m -- or --C(.dbd.O)(CH.sub.2).sub.n-1 --, wherein one of the methylene groups is optionally substituted with R.sup.7 ; Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 is selected from: C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl), heteroaryl, or heteroaryl(C.sub.1 .C.sub.6 alkyl); R.sup.9 is selected from: H, --SO.sub.2 R.sup.17, --SO.sub.2 NR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, aryl substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from: H, halogen, CF.sub.3, CN, NO.sub.2 , hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is --C(.dbd.O)--N(R.sup.13)--; X is --CH(R.sup.14)--CH(R.sup.15)--; R.sup.13 is H or CH.sub.3 ; R.sup.14 is selected from: H, C.sub.1 -C.sub.10 alkyl, aryl, or heteroaryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.15 is H or R.sup.16 ; Y is --COR.sup.19 ; R.sup.16 is selected from: --NH(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --N(R.sup.20)R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.19 is selected from: hydroxy, C.sub.1 -C.sub.10 alkoxy, methylcarbonyloxymethoxy-, ethylcarbonyloxymethoxy-, t-butylcarbonyloxymethoxy-, cyclohexylcarbonyloxymethoxy-, 1-(methylcarbonyloxy)ethoxy-, 1-(ethylcarbonyloxy)ethoxy-, 1-(t-butylcarbonyloxy)ethoxy-, 1-(cyclohexylcarbonyloxy)ethoxy-, i-propyloxycarbonyloxymethoxy-, t-butyloxycarbonyloxymethoxy-, 1-(i-propyloxycarbonyloxy)ethoxy-, 1-(cyclohexyloxycarbonyloxy)ethoxy-, 1-(t-butyloxycarbonyloxy)ethoxy-, dimethylaminoethoxy-, diethylaminoethoxy-, (5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or 1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-; R.sup.20 is H or CH.sub.3 ; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; and m is 0 or 1; n is 1-4; and t is 0 or 1.

›9.↳ 6A compound of claim 6 of the Formula IIc or IId: ##STR89## and pharmaceutically acceptable salt forms thereof, wherein: X.sub.1 and X.sub.3 are indepe…d2

A compound of claim 6 of the Formula IIc or IId: ##STR89## and pharmaceutically acceptable salt forms thereof, wherein: X.sub.1 and X.sub.3 are independently selected from nitrogen or carbon, provided that at least one of X.sub.1 and X.sub.3 is carbon; R.sup.1 is selected from: ##STR90## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH.sub.2, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.6 alkyl, and C.sub.3 -C.sub.7 cycloalkyl: U is --(CH.sub.2).sub.n --, --(CH.sub.2).sub.t Q(CH.sub.2).sub.m -- or --C(.dbd.O)(CH.sub.2).sub.n-1 --, wherein one of the methylene groups is optionally substituted with R.sup.7 ; Q is selected from 1,2-phenylene, 1,3-phenlylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 is selected from: C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl), heteroaryl, or heteroaryl(C.sub.1 -C.sub.6 alkyl); R.sup.9 is selected from: H, --SO.sub.2 R.sup.17, --SO.sub.2 NR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, aryl substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from H, halogen, CF.sub.3, CN, NO.sub.2, hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ;W is --C(.dbd.O)--N(R.sup.13)--; W is --C(.dbd.O)--N(R.sup.13)--; X is --CH(R.sup.14)--CH(R.sup.15); R.sup.13 is H or CH.sub.3 ; R.sup.14 is selected from: H, C.sub.1 -C.sub.10 alkyl, aryl, or heteroaryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.15 is H or R.sup.16 ; Y is --COR.sup.19 ; R.sup.16 is selected from: --N(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.0)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.19 is selected from: hydroxy, C.sub.1 -C.sub.10 alkoxy, methylcarbonyloxymethoxy-, ethylcarbonyloxymethoxy-, t-butylcarbonyloxymethoxy-, cyclohexylcarbonyloxymethoxy-, 1-(methylcarbonyloxy)ethoxy-, 1-(ethylcarbonyloxy)ethoxy-, 1-(t-butylcarbonyloxy)ethoxy-, 1-(cyclohexylcarbonyloxy)ethoxy-, i-propyloxycarbonyloxymethoxy-, t-butyloxycarbonyloxymethoxy-, 1-(i-propyloxycarbonyloxy)ethoxy-, 1-(cyclohexyloxycarbonyloxy)ethoxy-, 1-(t-butyloxycarbonyloxy)ethoxy-, dimethylaminoethoxy-, diethylaminoethoxy-, (5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or 1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-; R.sup.20 is H or CH.sub.3 ; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; and m is 0 or n 1; n is 1-4; and t is 0 or 1.

›10.↳ 6A compound of claim 6 of Formula Ib and enantiomeric or diasteriomeric forms thereof, and mixtures of enantiomeric or diasteriomeric forms thereof, an…d2

A compound of claim 6 of Formula Ib and enantiomeric or diasteriomeric forms thereof, and mixtures of enantiomeric or diasteriomeric forms thereof, and pharmaceutically acceptable salt forms thereof, selected from the group consisting of: 3-›3-›3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzylox ycarbonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2- (2,4,6-trimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzenes ulfonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2- (2,6-dichlorobenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(3,5-dime thylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2- (2,6-dimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dime thyl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazolin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2- (4-phenylbenzenesulfonylamino)propionic acid, 3-›3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(b enzyloxycarbonylamino)propionic acid, 3-›1-methyl-3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylam ino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(b enzenesulfonylamino)propionic acid, 3-›1-methyl-3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylam ino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid, 3-›3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(3 ,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-methyl-3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylam ino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2 ,6-dimethyl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-methyl-3-›3-(tetrahydropyrimid-2-ylamino)propyl!-indazol-6-ylcarbonyla mino!-2-(4-phenylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzyloxyc arbonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2 ,4,6-trimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzenesul fonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2 ,6-dichlorobenzenesulfonylamino)propionic acid, 3-›3-›3-imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(3,5-dimethy lisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2 ,6-dimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dimeth yl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazol-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(4 -phenylbenzenesulfonylamino)propionic acid, 3-›3-›3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzyloxyca rbonylamino)propionic acid, 3-›1-methyl-3-›3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2, 4,6-trimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(benzenesulf onylamino)propionic acid, 3-›1-methyl-3-›3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2, 6-dichlorobenzenesulfonylamino)propionic acid, 3-›3-›3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(3,5-dimethy lisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-methyl-3-›3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2, 6-dimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(2,6-dimethy l-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-methyl-3-›3-(pyridin-2-ylamino)propyl!indazol-6-ylcarbonylamino!-2-(4- phenylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzylox ycarbonylamino)propionic acid, 3-›1-methyl-3-(3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2- (2,4,6-trimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzenes ulfonylamino)propionic acid, 3-(1-methyl-3-›3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2- (2,6-dichlorobenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(3,5-dime thylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2- (2,6-dimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dime thyl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-methyl-3-(3-(imidazolin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2- (4-phenylbenzenesulfonylamino)propionic acid, 3-›3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(b enzyloxycarbonylamino)propionic acid, 3-›1-methyl-3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylam ino!-2-(2,4,6-trimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(b enzenesulfonylamino)propionic acid, 3-›1-methyl-3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylam ino!-2-(2,6-dichlorobenzenesulfonylamino)propionic acid, 3-›3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(3 ,5-dimethylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-methyl-3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylam ino!-2-(2,6-dimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2 ,6-dimethyl-4phenylbenzenesulfonylamino)propionic acid, 3-›1-methyl-3-›3-(tetrahydropyrimid-2-ylamino)propyl!indazol-7-ylcarbonylam ino!-2-(4-phenylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzyloxyc arbonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2 ,4,6-trimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzenesul fonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2 ,6-dichlorobenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(3,5-dimeth ylisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2 ,6-dimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dimeth yl-4-phenylbenzenesulfonylamino)propionic acid, 3-›1-methyl-3-›3-(imidazol-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(4 -phenylbenzenesulfonylamino)propionic acid, 3-›3-›3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzyloxyca rbonylamino)propionic acid, 3-›1-methyl-3-›3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2, 4,6-trimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(benzenesulf onylamino)propionic acid, 3-›1-methyl-3-›3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2, 6-dichlorobenzenesulfonylamino)propionic acid, 3-›3-›3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(3,5-dimethy lisoxazol-4-ylsulfonylamino)propionic acid, 3-›1-methyl-3-›3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2, 6-dimethylbenzenesulfonylamino)propionic acid, 3-›3-›3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(2,6-dimethy l-4-phenylbenzenesulfonylamino)propionic acid, and 3-›1-methyl-3-›3-(pyridin-2-ylamino)propyl!indazol-7-ylcarbonylamino!-2-(4- phenylbenzenesulfonylamino)propionic acid; and ester forms thereof, said esters being chosen from the group consisting of: methyl, ethyl, isopropyl, n-butyl, isobutyl, benzyl, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, tert-butylcarbonyloxymethyl, cyclohexylcarbonyloxymethyl, tert-butyloxycarbonyloxymethyl, dimethylaminoethyl, and diethylaminoethyl.

›11.independentA compound of Formula Ic: ##STR91## and pharmaceutically acceptable salt forms thereof, wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are independen…+3

A compound of Formula Ic: ##STR91## and pharmaceutically acceptable salt forms thereof, wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are independently selected from nitrogen or carbon provided that at least two of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are carbon; R.sup.1 is selected from: ##STR92## A and B are independently --CH.sub.2 --, --O--, --N(R.sup.2)--, or --C(.dbd.O)--; A.sup.1 and B.sup.1 are independently --CH.sub.2 -- or --N(R.sup.3)--; D is --N(R.sup.2)--, --O--, --S--, --C(.dbd.O)-- or --SO.sub.2 --; E--F is --C(R.sup.4).dbd.C(R.sup.5)--, --N.dbd.C(R.sup.4)--, --C(R.sup.4).dbd.N--, or --C(R.sup.4).sub.2 C(R.sup.5).sub.2 --; J, K, L and M are independently selected from --C(R.sup.4)--, --C(R.sup.5)-- or --N--, provided that at least one of J, K, L and M is not --N--; R.sup.2 is selected from: H, C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl; (C.sub.1 -C.sub.6 alkyl)aminocarbonyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)carbonyl, heteroarylcarbonyl, aryl C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyl, or arylcarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl, arylsulfonyl, aryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, aryloxycarbonyl, or aryl(C.sub.1 -C.sub.6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, CF.sub.3, and nitro; R.sup.3 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.4 and R.sup.5 are independently selected from: H, C.sub.1 -C.sub.4 alkoxy, NR.sup.2 R.sup.3, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)carbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl, arylcarbonyl, or alternatively, when substituents on adjacent atoms, R.sup.4 and R.sup.5 can be taken together with the carbon atoms to which they are attached to form a 5-7 membered carbocyclic or 5-7 membered heterocyclic aromatic or non-aromatic ring system, said carbocyclic or heterocyclic ring being optionally substituted with 0-2 groups selected from: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, cyano, amino, CF.sub.3, or NO.sub.2 ; U is selected from: --(CH.sub.2).sub.n --, --(CH.sub.2).sub.n (CR.sup.7 .dbd.CR.sup.8)(CH.sub.2).sub.m -- --(CH.sub.2).sub.n (C.tbd.C)(CH.sub.2).sub.m -- --(CH.sub.2).sub.t Q(CH.sub.2).sub.m -- --(CH.sub.2).sub.n O(CH.sub.2).sub.m --, --(CH.sub.2).sub.n N(R.sup.6)(CH.sub.2).sub.m --, --(CH.sub.2).sub.n C(.dbd.O)(CH.sub.2).sub.m --, --(CH.sub.2).sub.n (C.dbd.O)N(R.sup.6)(CH.sub.2).sub.m -- --(CH.sub.2).sub.n N(R.sup.6)(C.dbd.O)(CH.sub.2).sub.m --, or --(CH.sub.2).sub.n S(O).sub.p (CH.sub.2).sub.m --; wherein one of the methylene groups is optionally substituted with R.sup.7 ; Q is selected from 1,2-cycloalkylene, 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, 2,4-pyridinylene, or 3,4-pyridazinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 and R.sup.8 are independently selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.0 -C.sub.6 alkyl)-; R.sup.9 is selected from: H, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, --SO.sub.2 R.sup.17, --SO.sub.2 NR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.6 alkenyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, aryl substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from H, halogen, CF.sub.3, CN, NO.sub.2 , hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is selected from: --(C(R.sup.12).sub.2).sub.q C(.dbd.O)N(R.sup.13)--, or --C(.dbd.O)--N(R.sup.13)--(C(R.sup.12).sub.2).sub.q --; X is --C(R.sup.12)(R.sup.14)--C(R.sup.12)(R.sup.15)--; or alternatively, W and X can be taken together to be ##STR93## R.sup.12 is selected from: H, halogen, C.sub.1 -C.sub.6 alkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkynyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.10 cycloalkylalkyl, (C.sub.1 -C.sub.4 alkyl)carbonyl, aryl, or aryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.13 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkylmethyl, or aryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.14 is selected from: H, C.sub.1 -C.sub.6 alkylthio(C.sub.1 -C.sub.6 alkyl)-, aryl(C.sub.1 -C.sub.10 alkylthioalkyl)-, aryl(C.sub.1 -C.sub.10 alkoxyalkyl)-, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, or CONR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-1 R.sup.16 or 0-2 R.sup.11 ; R.sup.15 is selected from: H, R.sup.16, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 alkylaminoalkyl, C.sub.1 -C.sub.10 dialkylaminoalkyl, (C.sub.1 -C.sub.10 alkyl)carbonyl, aryl(C.sub.0 -C.sub.6 alkyl)carbonyl, C.sub.1 -C.sub.10 alkenyl, C.sub.1 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, SO.sub.2 R.sup.17, or SO.sub.2 NR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-2 R.sup.11 ; Y is selected from: --COR.sup.19, --SO.sub.3 H, --PO.sub.3 H, tetrazolyl, --CONHNHSO.sub.2 CF.sub.3, --CONHSO.sub.2 R.sup.17, --CONHSO.sub.2 NHR.sup.17, --NHCOCF.sub.3, --NHCONHSO.sub.2 R.sup.17, --NHSO.sub.2 R.sup.17, --OPO.sub.3 H.sub.2, --OSO.sub.3 H, --PO.sub.3 H.sub.2, --SO.sub.3 H, --SO.sub.2 NHCOR.sup.17, --SO.sub.2 NHCO.sub.2 R.sup.17, ##STR94## R.sup.16 is selected from: --N(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.18 is selected from: H, --C(.dbd.O)--O--R.sup.17, --C(.dbd.O)--R.sup.17, --C(.dbd.O)--NH--R.sup.17, --SO.sub.2 --R.sup.17, or --SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.19 is selected from hydroxy, C.sub.1 -C.sub.10 alkyloxy, C.sub.3 -C.sub.11 cycloalkyloxy, aryloxy, aryl(C.sub.1 -C.sub.6 alkoxy)-, C.sub.3 -C.sub.10 alkylcarbonyloxyalkyloxy, C.sub.3 -C.sub.10 alkoxycarbonyloxyalkyloxy, C.sub.2 -C.sub.10 alkoxycarbonylalkyloxy, C.sub.5 -C.sub.10 cycloalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonylalkyloxy, C.sub.7 -C.sub.11 aryloxycarbonylalkyloxy, C.sub.8 -C.sub.12 aryloxycarbonyloxyalkyloxy, C.sub.8 -C.sub.12 arylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 alkoxyalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 (5-alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C.sub.10 -C.sub.14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R.sup.11)(R.sup.12)N--(C.sub.1 -C.sub.10 alkoxy)-; R.sup.20 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; m is 0-4; n is 0-4; p is 0-2; q is 0-2; and r is 0-2; with the following provisos: (1) t, n, m and q are chosen such that the number of atoms connecting R.sup.1 and Y is in the range of 10-14; and (2) n and m are chosen such that the value of n plus m is greater than one unless U is --(CH.sub.2).sub.t Q(CH.sub.2).sub.m --.

›12.↳ 11A compound of claim 11 of the Formula Ic: ##STR95## and pharmaceutically acceptable salt forms thereof wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4…d2

A compound of claim 11 of the Formula Ic: ##STR95## and pharmaceutically acceptable salt forms thereof wherein: X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are independently selected from nitrogen or carbon provided that at least two of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are carbon; R.sup.1 is selected from: ##STR96## A and B are independently --CH.sub.2 --, --O--, --N(R.sup.2)--, or --C(.dbd.O)--; A.sup.1 and B.sup.1 are independently --CH.sub.2 -- or --N(R.sup.3)--; D is --N(R.sup.2)--, --O--, --S--, --C(.dbd.O)-- or --SO.sub.2 --; E--F is --C(R.sup.4).dbd.C(R.sup.5)--, --N.dbd.C(R.sup.4)--, --C(R.sup.4).dbd.N--, or --C(R.sup.4).sub.2 C(R.sup.5).sub.2 --; J, K, L and M are independently selected from: --C(R.sup.4)--, --C(R.sup.5)-- or --N--, provided that at least one of J, K, L and M is not --N--; R.sup.2 is selected from: H, C.sub.1 -C.sub.6 alkyl, (C.sub.1 -C.sub.6 alkyl)carbonyl, (C.sub.1 -C.sub.6 alkoxy)carbonyl, C.sub.1 -C.sub.6 alkylaminocarbonyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)carbonyl, heteroarylcarbonyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)carbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, aryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, heteroarylsulfonyl, heteroaryl(C.sub.1 -C.sub.6 alkyl)sulfonyl, aryloxycarbonyl, aryl(C.sub.1 -C.sub.6 alkoxy)carbonyl, wherein said aryl groups are substituted with 0-2 substituents selected from the group consisting of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, CF.sub.3, and nitro; R.sup.3 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.4 and R.sup.5 are independently selected from: H, C.sub.1 -C.sub.4 alkoxy, NR.sup.2 R.sup.3, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, C.sub.2 -C.sub.7 alkylcarbonyl, arylcarbonyl or alternatively, when substituents on adjacent atoms, R.sup.4 and R.sup.5 can be taken together with the carbon atoms to which they are attached to form a 5-7 membered carbocyclic or 5-7 membered heterocyclic aromatic or non-aromatic ring system, said carbocyclic or heterocyclic ring being optionally substituted with 0-2 groups selected from: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, cyano, amino, CF.sub.3, or NO.sub.2 ; U is selected from: --(CH.sub.2).sub.n --, --(CH.sub.2).sub.n (CR.sup.7 .dbd.CR.sup.8)(CH.sub.2).sub.m -- --(CH.sub.2).sub.t Q(CH.sub.2).sub.m --, --(CH.sub.2).sub.n O(CH.sub.2).sub.m --, --(CH.sub.2).sub.n N(R.sup.6)(CH.sub.2).sub.m --, --(CH.sub.2).sub.n C(.dbd.O)(CH.sub.2).sub.m --, or --(CH.sub.2).sub.n S(O).sub.p (CH.sub.2).sub.m --; wherein one of the methylene groups is optionally substituted with R.sup.7 ; Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 and R.sup.8 are independently selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.0 -C.sub.6 alkyl)-; R.sup.9 is selected from: H, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, --SO.sub.2 R.sup.17, --SO.sub.2 NR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.6 alkenyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, aryl substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from: H, halogen, CF.sub.3, CN, NO.sub.2, hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is --C(.dbd.O)--N(R.sup.13)--(C(R.sup.12).sub.2).sub.q --; X is --C(R.sup.12)(R.sup.14)--C(R.sup.12)(R.sup.15)--; alternatively, W and X can be taken together to be ##STR97## R.sup.12 is H or C.sub.1 -C.sub.6 alkyl; R.sup.13 is selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkylmethyl, or aryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.14 is selected from: H, C.sub.1 -C.sub.6 alkylthioalkyl, aryl(C.sub.1 -C.sub.10 alkylthioalkyl)-, aryl(C.sub.1 -C.sub.10 alkoxyalkyl)-, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.6 hydroxyalkyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-1 R.sup.16 or 0-2 R.sup.11 ; R.sup.15 is selected from: H, R.sup.16, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxyalkyl, C.sub.1 -C.sub.10 alkylaminoalkyl, C.sub.1 -C.sub.10 dialkylaminoalkyl, C.sub.1 -C.sub.10 alkylcarbonyl, aryl(C.sub.0 -C.sub.6 alkyl)carbonyl, C.sub.2 -C.sub.10 alkenyl, C.sub.2 -C.sub.10 alkynyl, C.sub.3 -C.sub.10 cycloalkyl, C.sub.3 -C.sub.10 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, aryl, heteroaryl, CO.sub.2 R.sup.17, C(.dbd.O)R.sup.17, CONR.sup.17 R.sup.20, SO.sub.2 R.sup.17, or SO.sub.2 NR.sup.17 R.sup.20, provided that any of the above alkyl, cycloalkyl, aryl or heteroaryl groups may be unsubstituted or substituted independently with 0-2 R.sup.11 ; Y is selected from: ##STR98## R.sup.16 is selected from: --N(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.18 is selected from: H, --C(.dbd.O)--O--R.sup.17, --C(.dbd.O)--R.sup.17, --C(.dbd.O)--NH--R.sup.17, --SO.sub.2 --R.sup.17, or --SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.19 is selected from: hydroxy, C.sub.1 -C.sub.10 alkyloxy, C.sub.3 -C.sub.11 cycloalkyloxy, C.sub.6 -C.sub.10 aryloxy, C.sub.7 -C.sub.11 aralkyloxy, C.sub.3 -C.sub.10 alkylcarbonyloxyalkyloxy, C.sub.3 -C.sub.10 alkoxycarbonyloxyalkyloxy, C.sub.2 -C.sub.10 alkoxycarbonylalkyloxy, C.sub.5 -C.sub.10 cycloalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonyloxyalkyloxy, C.sub.5 -C.sub.10 cycloalkoxycarbonylalkyloxy, C.sub.7 -C.sub.11 aryloxycarbonylalkyloxy, C.sub.8 -C.sub.12 aryloxycarbonyloxyalkyloxy, C.sub.8 -C.sub.12 arylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 alkoxyalkylcarbonyloxyalkyloxy, C.sub.5 -C.sub.10 (5-alkyl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, C.sub.10 -C.sub.14 (5-aryl-1,3-dioxa-cyclopenten-2-one-yl)methyloxy, or (R.sup.11)(R.sup.12)N--(C.sub.1 -C.sub.10 alkoxy)-; R.sup.20 selected from: H, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, or heteroaryl(C.sub.1 -C.sub.6 alkyl)-; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; m is 0-4; n is 0-4; t is 0-4; p is 0-2; q is 0-2; and r is 0-2.

›13.↳ 11A compound of claim 11 of the Formula IIe or IIf: ##STR99## and pharmaceutically acceptable salt forms thereof, wherein: R.sup.1 is selected from: ##S…d2

A compound of claim 11 of the Formula IIe or IIf: ##STR99## and pharmaceutically acceptable salt forms thereof, wherein: R.sup.1 is selected from: ##STR100## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH.sub.2, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.6 alkyl, and C.sub.3 -C.sub.7 cycloalkyl; U is --(CH.sub.2).sub.n --, --CH.sub.2).sub.t Q(CH.sub.2).sub.m -- or --(.dbd.O)(CH.sub.2).sub.n-1 --, wherein one of the methylene groups is optionally substituted with R.sup.7 ; Q is selected from 1,2-phenylene 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene; R.sup.6 is selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 is selected from: C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl), heteroaryl, or heteroaryl(C.sub.1 -C.sub.6 alkyl); R.sup.9 is selected from: H, --SO.sub.2 R.sup.17, --SO.sub.2 NR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, aryl substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from H, halogen, CF.sub.3, CN, NO.sub.2, hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is --C(.dbd.O)--N(R.sup.13)--; X is --CH(R.sup.14)--CH(R.sup.15)--; R.sup.13 is H or CH.sub.3 ; R.sup.14 is selected from: H, C.sub.1 -C.sub.10 alkyl, aryl, or heteroaryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.15 is H or R.sup.16 ; is --COR.sup.19 ; R.sup.16 is selected from: --NH(R.sup.20)--C(.dbd.O)--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --N(R.sup.20)R.sup.17 ; .sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.19 is selected from: hydroxy, C.sub.1 -C.sub.10 alkoxy, methylcarbonyloxymethoxy-, ethylcarbonyloxymethoxy-, t-butylcarbonyloxymethoxy-, cyclohexylcarbonyloxymethoxy-, 1-(methylcarbonyloxy)ethoxy-, 1-(ethylcarbonyloxy)ethoxy-, 1-(t-butylcarbonyloxy)ethoxy-, 1-(cyclohexylcarbonyloxy)ethoxy-, i-propyloxycarbonyloxymethoxy-, t-butyloxycarbonyloxymethoxy-, 1-(i-propyloxycarbonyloxy)ethoxy-, 1-(cyclohexyloxycarbonyloxy)ethoxy-, 1-(t-butyloxycarbonyloxy)ethoxy-, dimethylaminoethoxy-, diethylaminoethoxy-, (5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or 1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-; R.sup.20 is H or CH.sub.3 ; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; and m is 0 or 1; n is 1-4; and t is 0 or 1.

›14.↳ 11A compound of claim 11 of the Formula IIe or IIf: ##STR101## and pharmaceutically acceptable salt forms thereof, wherein: R.sup.1 is selected from: ##…d2

A compound of claim 11 of the Formula IIe or IIf: ##STR101## and pharmaceutically acceptable salt forms thereof, wherein: R.sup.1 is selected from: ##STR102## wherein the above heterocycles are optionally substituted with 0-2 substituents selected from the group consisting of: NH.sub.2, halogen, NO.sub.2, CN, CF.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.6 alkyl, and C.sub.3 -C.sub.7 cycloalkyl: U is --(CH.sub.2).sub.n --, --(CH.sub.2).sub.t Q(CH.sub.2).sub.m -- or --C(.dbd.O)(CH.sub.2).sub.n-1 --, wherein one of the methylene groups is optionally substituted with R.sup.7 ; Q is selected from 1,2-phenylene, 1,3-phenylene, 2,3-pyridinylene, 3,4-pyridinylene, or 2,4-pyridinylene; R.sup.6 selected from: H, C.sub.1 -C.sub.4 alkyl, or benzyl; R.sup.7 is selected from C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.4 -C.sub.11 cycloalkylalkyl, aryl, aryl(C.sub.1 -C.sub.6 alkyl), heteroaryl, or heteroaryl(C.sub.1 -C.sub.6 alkyl); R.sup.9 is selected from: H, --SO.sub.2 R.sup.17, --SO.sub.2 NR.sup.17 R.sup.20, C.sub.1 -C.sub.6 alkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.3 -C.sub.7 cycloalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, C.sub.4 -C.sub.11 cycloalkylalkyl substituted with 0-1 R.sup.15 or 0-1 R.sup.21, aryl substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21, or aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.15 or 0-2 R.sup.11 or 0-1 R.sup.21 ; R.sup.11 is selected from H, halogen, CF.sub.3, CN, NO.sub.2, hydroxy, NR.sup.2 R.sup.3, C.sub.1 -C.sub.4 alkyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkoxy substituted with 0-1 R.sup.21, aryl substituted with 0-1 R.sup.21, aryl(C.sub.1 -C.sub.6 alkyl)- substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkoxy)carbonyl substituted with 0-1 R.sup.21, (C.sub.1 -C.sub.4 alkyl)carbonyl substituted with 0-1 R.sup.21, C.sub.1 -C.sub.4 alkylsulfonyl substituted with 0-1 R.sup.21, or C.sub.1 -C.sub.4 alkylaminosulfonyl substituted with 0-1 R.sup.21 ; W is --C(.dbd.O)--N(R.sup.13)--; W is --C(.dbd.O)--N(R.sup.13)--; X is --CH(R.sup.14)--CH(R.sup.15)--; R.sup.13 is H or CH.sub.3 ; R.sup.14 is selected from: H, C.sub.1 -C.sub.10 alkyl, aryl, or heteroaryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.15 is H or R.sup.16 ; Y is --COR.sup.19 ; R.sup.16 is selected from: --NH(R.sup.20)--C(.dbd.O--O--R.sup.17, --N(R.sup.20)--C(.dbd.O)--R.sup.17, --N(R.sup.20)--C(.dbd.O)--NH--R.sup.17, --N(R.sup.20)SO.sub.2 --R.sup.17, or --N(R.sup.20)SO.sub.2 --NR.sup.20 R.sup.17 ; R.sup.17 is selected from: C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.11 cycloalkyl, aryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)aryl, heteroaryl(C.sub.1 -C.sub.6 alkyl)-, (C.sub.1 -C.sub.6 alkyl)heteroaryl, biaryl(C.sub.1 -C.sub.6 alkyl)-, heteroaryl, or aryl, wherein said aryl or heteroaryl groups are optionally substituted with 0-3 substituents selected from the group consisting of: C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, aryl, heteroaryl, halo, cyano, amino, CF.sub.3, and NO.sub.2 ; R.sup.19 is selected from: hydroxy, C.sub.1 -C.sub.10 alkoxy, methylcarbonyloxymethoxy-, ethylcarbonyloxymethoxy-, t-butylcarbonyloxymethoxy-, cyclohexylcarbonyloxymethoxy-, 1-(methylcarbonyloxy)ethoxy-, 1-(ethylcarbonyloxy)ethoxy-, 1-(t-butylcarbonyloxy)ethoxy-, 1-(cyclohexylcarbonyloxy)ethoxy-, i-propyloxycarbonyloxymethoxy-, t-butyloxycarbonyloxymethoxy-, 1-(i-propyloxycarbonyloxy)ethoxy-, 1-(cyclohexyloxycarbonyloxy)ethoxy-, 1-(t-butyloxycarbonyloxy)ethoxy-, dimethylaminoethoxy-, diethylaminoethoxy-, (5-methyl-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (5-(t-butyl)-1,3-dioxacyclopenten-2-on-4-yl)methoxy-, (1,3-dioxa-5-phenyl-cyclopenten-2-on-4-yl)methoxy-, or 1-(2-(2-methoxypropyl)carbonyloxy)ethoxy-; R.sup.20 is H or CH.sub.3 ; R.sup.21 is selected from COOH or NR.sup.6.sub.2 ; and m is 0 or 1; n is 1-4; and t is 0 or 1.

›15.independentmultiple · 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14A method for the treatment of cancer metastasis, diabetic retinopathy, neovascular glaucoma, thrombosis, restenosis, osteoporosis, or macular degenera…

›16.independentmultiple · 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of any one of claims 1-14.

Classifications

53 codes

IPC · International Patent Classification

Section C — Chemistry; metallurgy

C07D403/12
C07D401/12

USPC · US Patent Classification

514/211514/212540/575514/229.2544/224514/228.2540/597540/603548/122544/337540/602514/227548/127540/601514/256544/262544/182514/258548/312.1548/128546/244548/361.1540/596544/350544/371548/136544/295540/599544/67548/254544/96546/272.4540/545548/131540/554548/134540/600546/268.1548/146514/242544/361544/98544/238546/119548/255544/333544/179540/598514/253548/262.2546/278.1

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